JP7301337B2 - Compound and its manufacturing method - Google Patents

Description

The present invention relates to compounds and methods for producing them.

Diindolylbenzenes having a structure in which two indole ring skeletons are bonded to a benzene ring skeleton have various types according to the bonding positions of the two indole ring skeletons to the benzene ring skeleton. Such diindolylbenzenes are not only natural products, but are also known to be bioactive substances and electronic materials, and are an important group of compounds.

Among diindolylbenzenes, o-bis(3-indolyl)benzenes having a structure in which two indole ring skeletons are bonded to adjacent carbon atoms in the benzene ring skeleton at the C3 position also exhibit interesting activities. There is expected. However, the number of reports on the synthesis of this compound is extremely limited, and a method for obtaining the desired product by reacting hydroquinones and indoles in the presence of an acid catalyst (see Patent Document 1) is known. It is nothing more than

S. Koulouri et al. , Tetrahedron 61 (2005) 10894-10902

However, the method described in Non-Patent Document 1 requires hydroquinones having hydroxyl groups as reaction targets for indoles, and the diindolylbenzenes obtained always have hydroxyl groups in their structures, The types of diindolylbenzenes that can be produced have been limited.

An object of the present invention is to provide novel diindolylbenzenes and a method for producing the same.

The present invention provides a compound represented by the following general formula (3).

（式中、Ｒ^１及びＲ^２は、それぞれ独立に、水素原子、脂肪族基、アリール基、ヘテロアリール基、アリールアルキル基、アルキルアリール基又はトリアルキルシリル基であり、前記脂肪族基、アリール基、ヘテロアリール基、アリールアルキル基、アルキルアリール基又はトリアルキルシリル基中の１個又は２個以上の水素原子は、アルコキシ基、アリールオキシ基又はハロゲン原子で置換されていてもよく；
Ｒ^３、Ｒ^４、Ｒ^５及びＲ^６は、それぞれ独立に、水素原子又は水素原子以外の一価の基であり；
Ｒ^７及びＲ^８は、それぞれ独立に、水素原子、ハロゲン原子、脂肪族基、アリール基、アルコキシ基、アリールオキシ基、ヘテロアリール基、アリールアルキル基、アルキルアリール基又はトリアルキルシリル基であり、前記脂肪族基、アルコキシ基、アリールオキシ基、アリールアルキル基、アルキルアリール基又はトリアルキルシリル基が１個又は互いに隣接していない２個以上のメチレン基を有する場合、前記メチレン基は、酸素原子、硫黄原子、カルボニルオキシ基又はオキシカルボニル基で置換されていてもよく、前記脂肪族基、アリール基、アルコキシ基、アリールオキシ基、ヘテロアリール基、アリールアルキル基、アルキルアリール基又はトリアルキルシリル基中の１個又は２個以上の水素原子は、アルキル基、アリール基、アルコキシ基、アリールオキシ基又はハロゲン原子で置換されていてもよく；
Ｒ^９は、水素原子、ハロゲン原子、脂肪族基、アリール基、アルコキシ基、アリールオキシ基、ヘテロアリール基、アリールアルキル基、アルキルアリール基、トリアルキルシリル基又はフタルイミドイル基であり、前記脂肪族基、アルコキシ基、アリールオキシ基、アリールアルキル基、アルキルアリール基又はトリアルキルシリル基が１個又は互いに隣接していない２個以上のメチレン基を有する場合、前記メチレン基は、酸素原子、硫黄原子、カルボニルオキシ基又はオキシカルボニル基で置換されていてもよく、前記脂肪族基、アリール基、アルコキシ基、アリールオキシ基、ヘテロアリール基、アリールアルキル基、アルキルアリール基又はトリアルキルシリル基中の１個又は２個以上の水素原子は、アルキル基、アリール基、アルコキシ基、アリールオキシ基又はハロゲン原子で置換されていてもよく；
２個のＲ^１、Ｒ^２、Ｒ^３、Ｒ^４、Ｒ^５及びＲ^６は、それぞれ互いに同一でも異なっていてもよく；
同一の環骨格に結合している、Ｒ^１、Ｒ^２、Ｒ^３、Ｒ^４、Ｒ^５及びＲ^６のうち、２個以上が有機基である場合、これら２個以上の有機基は、相互に結合して環を形成していてもよく；
Ｒ^７、Ｒ^８及びＲ^９のうち、２個以上が有機基である場合、これら２個以上の有機基は、相互に結合して環を形成していてもよい。）

(wherein R ¹ and R ² are each independently a hydrogen atom, an aliphatic group, an aryl group, a heteroaryl group, an arylalkyl group, an alkylaryl group or a trialkylsilyl group; one or more hydrogen atoms in the group, heteroaryl group, arylalkyl group, alkylaryl group or trialkylsilyl group may be replaced by an alkoxy group, an aryloxy group or a halogen atom;
R ³ , R ⁴ , R ⁵ and R ⁶ are each independently a hydrogen atom or a monovalent group other than a hydrogen atom;
^R7 and ^R8 are each independently a hydrogen atom, a halogen atom, an aliphatic group, an aryl group, an alkoxy group, an aryloxy group, a heteroaryl group, an arylalkyl group, an alkylaryl group or a trialkylsilyl group; When the aliphatic group, alkoxy group, aryloxy group, arylalkyl group, alkylaryl group or trialkylsilyl group has one or two or more methylene groups that are not adjacent to each other, the methylene group is an oxygen atom. , a sulfur atom, a carbonyloxy group or an oxycarbonyl group, the aliphatic group, aryl group, alkoxy group, aryloxy group, heteroaryl group, arylalkyl group, alkylaryl group or trialkylsilyl group one or more hydrogen atoms in may be substituted with an alkyl group, an aryl group, an alkoxy group, an aryloxy group or a halogen atom;
^R9 is a hydrogen atom, a halogen atom, an aliphatic group, an aryl group, an alkoxy group, an aryloxy group, a heteroaryl group, an arylalkyl group, an alkylaryl group, a trialkylsilyl group or a phthalimidoyl group, and the aliphatic When a group, an alkoxy group, an aryloxy group, an arylalkyl group, an alkylaryl group or a trialkylsilyl group has one or two or more methylene groups that are not adjacent to each other, the methylene groups are oxygen atoms, sulfur atoms , a carbonyloxy group or an oxycarbonyl group, and one of the aliphatic groups, aryl groups, alkoxy groups, aryloxy groups, heteroaryl groups, arylalkyl groups, alkylaryl groups and trialkylsilyl groups one or more hydrogen atoms may be replaced by alkyl groups, aryl groups, alkoxy groups, aryloxy groups or halogen atoms;
two R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁶ may be the same or different;
When two or more of R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁶ bonded to the same ring skeleton are organic groups, these two or more organic groups are may be linked to form a ring;
When two or more of R ⁷ , R ⁸ and R ⁹ are organic groups, these two or more organic groups may combine with each other to form a ring. )

In the compound represented by the general formula (3) of the present invention, R ¹ is a hydrogen atom, an alkyl group, an aryl group, an arylalkyl group or an alkylaryl group, and the alkyl group, aryl group or arylalkyl one or more hydrogen atoms in the group or alkylaryl group may be substituted with a halogen atom or an alkoxy group, and said ^R2 is a hydrogen atom, an alkyl group, an aryl group or an alkylaryl group; , one or more hydrogen atoms in the alkyl group, aryl group or alkylaryl group may be substituted with a halogen atom or an alkoxy group, and the R ³ , R ⁴ , R ⁵ and R ⁶ are , are each independently preferably a hydrogen atom, an alkyl group, an alkoxy group or a halogen atom.

In the compound represented by the general formula (3) of the present invention, R ¹ is a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, a phenyl group or a benzyl group, and 1 to 3 one hydrogen atom may be substituted with an alkyl group or alkoxy group having 1 to 3 carbon atoms or a halogen atom, and said R ² is a hydrogen atom, an alkyl group having 1 to 5 carbon atoms or a phenyl group, 1 to 3 hydrogen atoms in the phenyl group may be substituted with an alkyl group or alkoxy group having 1 to 3 carbon atoms or a halogen atom, and the R ³ , R ⁴ , R ⁵ and R ⁶ are Each independently is preferably a hydrogen atom, an alkyl or alkoxy group having 1 to 3 carbon atoms, or a halogen atom.
The present invention also provides a compound represented by the following general formula (3a).

（式中、Ｒ^１及びＲ^２は、それぞれ独立に、水素原子、脂肪族基、アリール基、ヘテロアリール基、アリールアルキル基、アルキルアリール基又はトリアルキルシリル基であり、前記脂肪族基、アリール基、ヘテロアリール基、アリールアルキル基、アルキルアリール基又はトリアルキルシリル基中の１個又は２個以上の水素原子は、アルコキシ基、アリールオキシ基又はハロゲン原子で置換されていてもよく；
Ｒ^３、Ｒ^４、Ｒ^５及びＲ^６は、それぞれ独立に、水素原子又は水素原子以外の一価の基であり；
Ｒ^７及びＲ^８は、それぞれ独立に、水素原子、ハロゲン原子、脂肪族基、アリール基、アルコキシ基、アリールオキシ基、ヘテロアリール基、アリールアルキル基、アルキルアリール基又はトリアルキルシリル基であり、前記脂肪族基、アルコキシ基、アリールオキシ基、アリールアルキル基、アルキルアリール基又はトリアルキルシリル基が１個又は互いに隣接していない２個以上のメチレン基を有する場合、前記メチレン基は、酸素原子、硫黄原子、カルボニルオキシ基又はオキシカルボニル基で置換されていてもよく、前記脂肪族基、アリール基、アルコキシ基、アリールオキシ基、ヘテロアリール基、アリールアルキル基、アルキルアリール基又はトリアルキルシリル基中の１個又は２個以上の水素原子は、アルキル基、アリール基、アルコキシ基、アリールオキシ基又はハロゲン原子で置換されていてもよく；
Ｒ^９は、水素原子、ハロゲン原子、脂肪族基、アリール基、アルコキシ基、アリールオキシ基、ヘテロアリール基、アリールアルキル基、アルキルアリール基、トリアルキルシリル基又はフタルイミドイル基であり、前記脂肪族基、アルコキシ基、アリールオキシ基、アリールアルキル基、アルキルアリール基又はトリアルキルシリル基が１個又は互いに隣接していない２個以上のメチレン基を有する場合、前記メチレン基は、酸素原子、硫黄原子、カルボニルオキシ基又はオキシカルボニル基で置換されていてもよく、前記脂肪族基、アリール基、アルコキシ基、アリールオキシ基、ヘテロアリール基、アリールアルキル基、アルキルアリール基又はトリアルキルシリル基中の１個又は２個以上の水素原子は、アルキル基、アリール基、アルコキシ基、アリールオキシ基又はハロゲン原子で置換されていてもよく；
２個のＲ^１、Ｒ^２、Ｒ^３、Ｒ^４、Ｒ^５及びＲ^６は、それぞれ互いに同一でも異なっていてもよく；
同一の環骨格に結合している、Ｒ^１、Ｒ^２、Ｒ^３、Ｒ^４、Ｒ^５及びＲ^６のうち、２個以上が有機基である場合、これら２個以上の有機基は、相互に結合して環を形成していてもよく；
Ｒ^７、Ｒ^８及びＲ^９のうち、２個以上が有機基である場合、これら２個以上の有機基は、相互に結合して環を形成していてもよい。）
また、本発明は、下記一般式（１）で表される化合物と、下記一般式（２）で表される化合物とを、酸触媒の共存下で反応させ、下記一般式（３）で表される化合物を得る、化合物の製造方法を提供する。

(wherein R ¹ and R ² are each independently a hydrogen atom, an aliphatic group, an aryl group, a heteroaryl group, an arylalkyl group, an alkylaryl group or a trialkylsilyl group; one or more hydrogen atoms in the group, heteroaryl group, arylalkyl group, alkylaryl group or trialkylsilyl group may be replaced by an alkoxy group, an aryloxy group or a halogen atom;
R ³ , R ⁴ , R ⁵ and R ⁶ are each independently a hydrogen atom or a monovalent group other than a hydrogen atom;
^R7 and ^R8 are each independently a hydrogen atom, a halogen atom, an aliphatic group, an aryl group, an alkoxy group, an aryloxy group, a heteroaryl group, an arylalkyl group, an alkylaryl group or a trialkylsilyl group; When the aliphatic group, alkoxy group, aryloxy group, arylalkyl group, alkylaryl group or trialkylsilyl group has one or two or more methylene groups that are not adjacent to each other, the methylene group is an oxygen atom. , a sulfur atom, a carbonyloxy group or an oxycarbonyl group, the aliphatic group, aryl group, alkoxy group, aryloxy group, heteroaryl group, arylalkyl group, alkylaryl group or trialkylsilyl group one or more hydrogen atoms in may be substituted with an alkyl group, an aryl group, an alkoxy group, an aryloxy group or a halogen atom;
^R9 is a hydrogen atom, a halogen atom, an aliphatic group, an aryl group, an alkoxy group, an aryloxy group, a heteroaryl group, an arylalkyl group, an alkylaryl group, a trialkylsilyl group or a phthalimidoyl group, and the aliphatic When the group, alkoxy group, aryloxy group, arylalkyl group, alkylaryl group or trialkylsilyl group has one or two or more non-adjacent methylene groups, the methylene groups are oxygen atoms, sulfur atoms , a carbonyloxy group or an oxycarbonyl group, and one of the aliphatic groups, aryl groups, alkoxy groups, aryloxy groups, heteroaryl groups, arylalkyl groups, alkylaryl groups and trialkylsilyl groups one or more hydrogen atoms may be replaced by an alkyl group, an aryl group, an alkoxy group, an aryloxy group or a halogen atom;
two R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁶ may be the same or different;
When two or more of R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁶ bonded to the same ring skeleton are organic groups, these two or more organic groups are may be linked to form a ring;
When two or more of R ⁷ , R ⁸ and R ⁹ are organic groups, these two or more organic groups may combine with each other to form a ring. )
Further, in the present invention, a compound represented by the following general formula (1) and a compound represented by the following general formula (2) are reacted in the presence of an acid catalyst, and a compound represented by the following general formula (3) is obtained. Provided is a method for producing a compound that yields a compound obtained by

（式中、Ｒ^１及びＲ^２は、それぞれ独立に、水素原子、脂肪族基、アリール基、ヘテロアリール基、アリールアルキル基、アルキルアリール基又はトリアルキルシリル基であり、前記脂肪族基、アリール基、ヘテロアリール基、アリールアルキル基、アルキルアリール基又はトリアルキルシリル基中の１個又は２個以上の水素原子は、アルコキシ基、アリールオキシ基又はハロゲン原子で置換されていてもよく；
Ｒ^３、Ｒ^４、Ｒ^５及びＲ^６は、それぞれ独立に、水素原子又は水素原子以外の一価の基であり；
Ｒ^７及びＲ^８は、それぞれ独立に、水素原子、ハロゲン原子、脂肪族基、アリール基、アルコキシ基、アリールオキシ基、ヘテロアリール基、アリールアルキル基、アルキルアリール基又はトリアルキルシリル基であり、前記脂肪族基、アルコキシ基、アリールオキシ基、アリールアルキル基、アルキルアリール基又はトリアルキルシリル基が１個又は互いに隣接していない２個以上のメチレン基を有する場合、前記メチレン基は、酸素原子、硫黄原子、カルボニルオキシ基又はオキシカルボニル基で置換されていてもよく、前記脂肪族基、アリール基、アルコキシ基、アリールオキシ基、ヘテロアリール基、アリールアルキル基、アルキルアリール基又はトリアルキルシリル基中の１個又は２個以上の水素原子は、アルキル基、アリール基、アルコキシ基、アリールオキシ基又はハロゲン原子で置換されていてもよく；
Ｒ^９は、水素原子、ハロゲン原子、脂肪族基、アリール基、アルコキシ基、アリールオキシ基、ヘテロアリール基、アリールアルキル基、アルキルアリール基、トリアルキルシリル基又はフタルイミドイル基であり、前記脂肪族基、アルコキシ基、アリールオキシ基、アリールアルキル基、アルキルアリール基又はトリアルキルシリル基が１個又は互いに隣接していない２個以上のメチレン基を有する場合、前記メチレン基は、酸素原子、硫黄原子、カルボニルオキシ基又はオキシカルボニル基で置換されていてもよく、前記脂肪族基、アリール基、アルコキシ基、アリールオキシ基、ヘテロアリール基、アリールアルキル基、アルキルアリール基又はトリアルキルシリル基中の１個又は２個以上の水素原子は、アルキル基、アリール基、アルコキシ基、アリールオキシ基又はハロゲン原子で置換されていてもよく；
２個のＲ^１、Ｒ^２、Ｒ^３、Ｒ^４、Ｒ^５及びＲ^６は、それぞれ互いに同一でも異なっていてもよく；
同一の環骨格に結合している、Ｒ^１、Ｒ^２、Ｒ^３、Ｒ^４、Ｒ^５及びＲ^６のうち、２個以上が有機基である場合、これら２個以上の有機基は、相互に結合して環を形成していてもよく；
Ｒ^７、Ｒ^８及びＲ^９のうち、２個以上が有機基である場合、これら２個以上の有機基は、相互に結合して環を形成していてもよい。）

(wherein R ¹ and R ² are each independently a hydrogen atom, an aliphatic group, an aryl group, a heteroaryl group, an arylalkyl group, an alkylaryl group or a trialkylsilyl group; one or more hydrogen atoms in the group, heteroaryl group, arylalkyl group, alkylaryl group or trialkylsilyl group may be replaced by an alkoxy group, an aryloxy group or a halogen atom;
R ³ , R ⁴ , R ⁵ and R ⁶ are each independently a hydrogen atom or a monovalent group other than a hydrogen atom;
^R7 and ^R8 are each independently a hydrogen atom, a halogen atom, an aliphatic group, an aryl group, an alkoxy group, an aryloxy group, a heteroaryl group, an arylalkyl group, an alkylaryl group or a trialkylsilyl group; When the aliphatic group, alkoxy group, aryloxy group, arylalkyl group, alkylaryl group or trialkylsilyl group has one or two or more methylene groups that are not adjacent to each other, the methylene group is an oxygen atom. , a sulfur atom, a carbonyloxy group or an oxycarbonyl group, the aliphatic group, aryl group, alkoxy group, aryloxy group, heteroaryl group, arylalkyl group, alkylaryl group or trialkylsilyl group one or more hydrogen atoms in may be substituted with an alkyl group, an aryl group, an alkoxy group, an aryloxy group or a halogen atom;
^R9 is a hydrogen atom, a halogen atom, an aliphatic group, an aryl group, an alkoxy group, an aryloxy group, a heteroaryl group, an arylalkyl group, an alkylaryl group, a trialkylsilyl group or a phthalimidoyl group, and the aliphatic When the group, alkoxy group, aryloxy group, arylalkyl group, alkylaryl group or trialkylsilyl group has one or two or more non-adjacent methylene groups, the methylene groups are oxygen atoms, sulfur atoms , a carbonyloxy group or an oxycarbonyl group, and one of the aliphatic groups, aryl groups, alkoxy groups, aryloxy groups, heteroaryl groups, arylalkyl groups, alkylaryl groups and trialkylsilyl groups one or more hydrogen atoms may be replaced by an alkyl group, an aryl group, an alkoxy group, an aryloxy group or a halogen atom;
two R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁶ may be the same or different;
When two or more of R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁶ bonded to the same ring skeleton are organic groups, these two or more organic groups are may be linked to form a ring;
When two or more of R ⁷ , R ⁸ and R ⁹ are organic groups, these two or more organic groups may combine with each other to form a ring. )

INDUSTRIAL APPLICABILITY According to the present invention, novel diindolylbenzenes and a method for producing the same are provided.

<<Compound (3)>>
A compound according to one embodiment of the present invention (in this specification, may be referred to as "compound (3)") is represented by the following general formula (3).

（式中、Ｒ^１及びＲ^２は、それぞれ独立に、水素原子、脂肪族基、アリール基、ヘテロアリール基、アリールアルキル基、アルキルアリール基又はトリアルキルシリル基であり、前記脂肪族基、アリール基、ヘテロアリール基、アリールアルキル基、アルキルアリール基又はトリアルキルシリル基中の１個又は２個以上の水素原子は、アルコキシ基、アリールオキシ基又はハロゲン原子で置換されていてもよく；
Ｒ^３、Ｒ^４、Ｒ^５及びＲ^６は、それぞれ独立に、水素原子又は水素原子以外の一価の基であり；
Ｒ^７及びＲ^８は、それぞれ独立に、水素原子、ハロゲン原子、脂肪族基、アリール基、アルコキシ基、アリールオキシ基、ヘテロアリール基、アリールアルキル基、アルキルアリール基又はトリアルキルシリル基であり、前記脂肪族基、アルコキシ基、アリールオキシ基、アリールアルキル基、アルキルアリール基又はトリアルキルシリル基が１個又は互いに隣接していない２個以上のメチレン基を有する場合、前記メチレン基は、酸素原子、硫黄原子、カルボニルオキシ基又はオキシカルボニル基で置換されていてもよく、前記脂肪族基、アリール基、アルコキシ基、アリールオキシ基、ヘテロアリール基、アリールアルキル基、アルキルアリール基又はトリアルキルシリル基中の１個又は２個以上の水素原子は、アルキル基、アリール基、アルコキシ基、アリールオキシ基又はハロゲン原子で置換されていてもよく；
Ｒ^９は、水素原子、ハロゲン原子、脂肪族基、アリール基、アルコキシ基、アリールオキシ基、ヘテロアリール基、アリールアルキル基、アルキルアリール基、トリアルキルシリル基又はフタルイミドイル基であり、前記脂肪族基、アルコキシ基、アリールオキシ基、アリールアルキル基、アルキルアリール基又はトリアルキルシリル基が１個又は互いに隣接していない２個以上のメチレン基を有する場合、前記メチレン基は、酸素原子、硫黄原子、カルボニルオキシ基又はオキシカルボニル基で置換されていてもよく、前記脂肪族基、アリール基、アルコキシ基、アリールオキシ基、ヘテロアリール基、アリールアルキル基、アルキルアリール基又はトリアルキルシリル基中の１個又は２個以上の水素原子は、アルキル基、アリール基、アルコキシ基、アリールオキシ基又はハロゲン原子で置換されていてもよく；
２個のＲ^１、Ｒ^２、Ｒ^３、Ｒ^４、Ｒ^５及びＲ^６は、それぞれ互いに同一でも異なっていてもよく；
同一の環骨格に結合している、Ｒ^１、Ｒ^２、Ｒ^３、Ｒ^４、Ｒ^５及びＲ^６のうち、２個以上が有機基である場合、これら２個以上の有機基は、相互に結合して環を形成していてもよく；
Ｒ^７、Ｒ^８及びＲ^９のうち、２個以上が有機基である場合、これら２個以上の有機基は、相互に結合して環を形成していてもよい。）

(wherein R ¹ and R ² are each independently a hydrogen atom, an aliphatic group, an aryl group, a heteroaryl group, an arylalkyl group, an alkylaryl group or a trialkylsilyl group; one or more hydrogen atoms in the group, heteroaryl group, arylalkyl group, alkylaryl group or trialkylsilyl group may be replaced by an alkoxy group, an aryloxy group or a halogen atom;
R ³ , R ⁴ , R ⁵ and R ⁶ are each independently a hydrogen atom or a monovalent group other than a hydrogen atom;
^R7 and ^R8 are each independently a hydrogen atom, a halogen atom, an aliphatic group, an aryl group, an alkoxy group, an aryloxy group, a heteroaryl group, an arylalkyl group, an alkylaryl group or a trialkylsilyl group; When the aliphatic group, alkoxy group, aryloxy group, arylalkyl group, alkylaryl group or trialkylsilyl group has one or two or more methylene groups that are not adjacent to each other, the methylene group is an oxygen atom. , a sulfur atom, a carbonyloxy group or an oxycarbonyl group, the aliphatic group, aryl group, alkoxy group, aryloxy group, heteroaryl group, arylalkyl group, alkylaryl group or trialkylsilyl group one or more hydrogen atoms in may be substituted with an alkyl group, an aryl group, an alkoxy group, an aryloxy group or a halogen atom;
^R9 is a hydrogen atom, a halogen atom, an aliphatic group, an aryl group, an alkoxy group, an aryloxy group, a heteroaryl group, an arylalkyl group, an alkylaryl group, a trialkylsilyl group or a phthalimidoyl group, and the aliphatic When the group, alkoxy group, aryloxy group, arylalkyl group, alkylaryl group or trialkylsilyl group has one or two or more non-adjacent methylene groups, the methylene groups are oxygen atoms, sulfur atoms , a carbonyloxy group or an oxycarbonyl group, and one of the aliphatic groups, aryl groups, alkoxy groups, aryloxy groups, heteroaryl groups, arylalkyl groups, alkylaryl groups and trialkylsilyl groups one or more hydrogen atoms may be replaced by an alkyl group, an aryl group, an alkoxy group, an aryloxy group or a halogen atom;
two R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁶ may be the same or different;
When two or more of R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁶ bonded to the same ring skeleton are organic groups, these two or more organic groups are may be linked to form a ring;
When two or more of R ⁷ , R ⁸ and R ⁹ are organic groups, these two or more organic groups may combine with each other to form a ring. )

Compound (3) is a diindolylbenzene having a structure in which two indole ring skeletons are bonded to one benzene ring skeleton. are o-bis(3-indolyl)benzenes having a structure attached to adjacent carbon atoms in a single benzene ring skeleton.
Compound (3) is a group of compounds having various functional groups in two indole ring skeletons and one benzene ring skeleton, and has diversity in structure. It can be easily manufactured without being overly restrictive.

Compound (3) has multiple stereoisomers, and all stereoisomers are included in this embodiment.

In general formula (3), R ¹ and R ² are each independently a hydrogen atom, an aliphatic group, an aryl group, a heteroaryl group, an arylalkyl group, an alkylaryl group or a trialkylsilyl group.
R ¹ and R ² may be the same or different.

The aliphatic group for R ¹ and R ² may be either a saturated aliphatic group or an unsaturated aliphatic group.
The aliphatic group for R ¹ and R ² may be linear, branched or cyclic (aliphatic cyclic group), preferably linear or branched.
The number of carbon atoms in the aliphatic group for R ¹ and R ² is preferably 1-30, more preferably 1-20.

Among the aliphatic groups for R ¹ and R ² , the linear or branched saturated aliphatic group (alkyl group) preferably has 1 to 10 carbon atoms. Examples of such alkyl groups include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, 1-methylbutyl group, n-hexyl group, 2-methylpentyl group, 3-methylpentyl group, 2,2-dimethylbutyl group, 2,3-dimethylbutyl group, n-heptyl group , 2-methylhexyl group, 3-methylhexyl group, 2,2-dimethylpentyl group, 2,3-dimethylpentyl group, 2,4-dimethylpentyl group, 3,3-dimethylpentyl group, 3-ethylpentyl group , 2,2,3-trimethylbutyl group, n-octyl group, isooctyl group, nonyl group, decyl group and the like.
More preferably, the linear or branched alkyl group has 1 to 6 carbon atoms.

Among the aliphatic groups for R ¹ and R ² , the cyclic alkyl group (cycloalkyl group) may be either monocyclic or polycyclic.
The number of carbon atoms in the cyclic alkyl group is 3 or more, preferably 3-10. Examples of such alkyl groups include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, norbornyl, isobornyl, 1-adamantyl, 2- adamantyl group, tricyclodecyl group and the like.
More preferably, the cyclic alkyl group has 5 to 10 carbon atoms.

The alkyl group is a mixture of a linear or branched chain structure and a cyclic structure, such as a cyclopentylmethyl group, 1-cyclopentylethyl group, cyclohexylmethyl group, and 1-cyclohexylethyl group. may Here, the chain structure and the cyclic structure include, for example, the alkyl group, or a group having a structure in which one or more hydrogen atoms are removed from the alkyl group.
The number of carbon atoms in such an alkyl group having both a chain structure and a cyclic structure is preferably 4-10.

Among the aliphatic groups for R ¹ and R ² , the unsaturated aliphatic group includes, for example, in the alkyl group, one or more single bonds (C—C) between carbon atoms are double bonds (C═C ) or a structure substituted with a triple bond (C≡C). The number and positions of these unsaturated bonds (double bonds and triple bonds) in the unsaturated aliphatic group are not particularly limited, and the unsaturated aliphatic group has both double bonds and triple bonds. good too.

In the unsaturated aliphatic group as R ¹ , the bond between the carbon atom bonded to the nitrogen atom at the 1-position constituting the indole ring skeleton and the carbon atom adjacent to this carbon atom is unsaturated It is preferably not a bond, and the smaller the number of unsaturated bonds, the better.
In the unsaturated aliphatic group as R ² , the bond between the carbon atom bonded to the 2-position carbon atom constituting the indole ring skeleton and the carbon atom adjacent to this carbon atom is unsaturated It is preferably not a bond, and the smaller the number of unsaturated bonds, the better.

The unsaturated aliphatic groups for R ¹ and R ² are preferably linear, branched or cyclic alkenyl groups, or linear, branched or cyclic alkynyl groups.

Examples of the alkenyl group for R ¹ and R ² include vinyl group (ethenyl group), allyl group (2-propenyl group, allyl group), cyclohexenyl group and the like.
The alkenyl group preferably has 2 to 6 carbon atoms.

The aryl groups in R ¹ and R ² may be either monocyclic or polycyclic.
The aryl group preferably has 6 to 12 carbon atoms, and examples of such aryl groups include phenyl, 1-naphthyl, and 2-naphthyl groups.

Examples of the arylalkyl group (aralkyl group) for R ¹ and R ² include a monovalent group having a structure in which the aryl group is bonded to an alkylene group.
Examples of the alkylene group include groups having a structure in which one hydrogen atom is removed from the alkyl group as R ¹ .
The arylalkyl group preferably has 7 to 15 carbon atoms. Examples of such arylalkyl groups include benzyl group (phenylmethyl group), 1-phenylethyl group (phenethyl group), 2-phenyl An ethyl group etc. are mentioned.

The alkylaryl group for R ¹ and R ² includes, for example, 4-methylphenyl group, 3-methylphenyl group, 2-methylphenyl group, etc., in which one hydrogen atom of the aryl group is substituted with an alkyl group. A monovalent group having a structure can be mentioned.
Examples of the alkyl group substituted with a hydrogen atom include the same alkyl groups as the alkyl groups for R ¹ and R ² .
The alkylaryl group preferably has 7 to 15 carbon atoms.

The heteroaryl group for R ¹ and R ² is not particularly limited as long as it has one or more heteroatoms as atoms constituting the aromatic heterocyclic ring skeleton, and may be either monocyclic or polycyclic. may be The heteroaryl group may have, for example, a structure in which a ring other than the aromatic heterocyclic ring is condensed to an aromatic heterocyclic ring, and the ring other than the aromatic heterocyclic ring includes an aliphatic hydrocarbon ring, A hydrocarbon ring such as an aromatic hydrocarbon ring; a non-aromatic heterocyclic ring (a ring having one or more hetero atoms as atoms constituting the ring skeleton and having no aromaticity), and the like.

The heteroaryl group for R ¹ and R ² preferably has 3 to 10 atoms, more preferably 4 to 8 atoms constituting the aromatic heterocyclic skeleton. When the heteroaryl group has a structure in which a ring other than an aromatic heterocyclic ring is condensed to an aromatic heterocyclic ring, the above-mentioned "atoms constituting the aromatic heterocyclic ring skeleton" are fused to the aromatic heterocyclic ring. Atoms constituting ring skeletons of rings other than the ringing aromatic heterocycle shall not be included. Further, when the heteroaryl group has a structure in which polycyclic aromatic heterocycles are condensed with each other, the above-mentioned "number of atoms constituting the aromatic heterocyclic skeleton" means the total number of atoms constituting the ring skeleton of the aromatic heterocyclic ring.

Examples of the heteroatom constituting the aromatic heterocyclic skeleton of the heteroaryl group in R ¹ and R ² include a sulfur atom, a nitrogen atom, an oxygen atom, a selenium atom and a phosphorus atom.
The number of heteroatoms constituting one aromatic heterocyclic skeleton is not particularly limited, but is preferably 1 to 2, more preferably 1. When the number of said heteroatoms constituting one aromatic heterocyclic ring skeleton is 2 or more, the plurality of heteroatoms may all be the same, all may be different, or one Only the parts may be the same.

The heteroaryl group for R ¹ and R ² is, for example, a group having a structure in which one hydrogen atom bonded to a carbon atom constituting the ring skeleton is removed from an aromatic heterocyclic compound. Preferred aromatic heterocyclic compounds include, for example, sulfur-containing aromatic heterocyclic compounds (compounds having one or more sulfur atoms as atoms constituting the aromatic heterocyclic skeleton), nitrogen-containing aromatic heterocyclic rings Compounds (compounds having 1 or 2 or more nitrogen atoms as atoms constituting the aromatic heterocyclic skeleton), oxygen-containing aromatic heterocyclic compounds (1 or 2 or more atoms constituting the aromatic heterocyclic skeleton compound having an oxygen atom of), a compound having two heteroatoms different from each other selected from a sulfur atom, a nitrogen atom and an oxygen atom as atoms constituting an aromatic heterocyclic skeleton, and the like.

Examples of the sulfur-containing aromatic heterocyclic compound include thiophene and benzothiophene.
Examples of the nitrogen-containing aromatic heterocyclic compound include pyrrole, imidazole, pyrazole, pyridine, pyrazine, pyrimidine, pyridazine, triazine, indole, isoindole, benzimidazole, purine, indazole, quinoline, isoquinoline, quinoxaline, quinazoline, cinnoline. etc.
Examples of the oxygen-containing aromatic heterocyclic compound include furan, benzofuran (1-benzofuran), isobenzofuran (2-benzofuran) and the like.
Examples of compounds having two different heteroatoms as atoms constituting the aromatic heterocyclic skeleton include oxazole, isoxazole, thiazole, benzoxazole, benzisoxazole, and benzothiazole.

Examples of the three alkyl groups in the trialkylsilyl group for R ¹ and R ² include the same alkyl groups as the alkyl groups for R ¹ and R ² .
All three alkyl groups in the trialkylsilyl group may be the same, all may be different, or only two may be the same.
The trialkylsilyl group is preferably a trimethylsilyl group, a triethylsilyl group or a triisopropylsilyl group.

One or more hydrogen atoms in the aliphatic group, aryl group, heteroaryl group, arylalkyl group, alkylaryl group or trialkylsilyl group for R ¹ and R ² are alkoxy groups, aryloxy groups or It may be substituted with a halogen atom.
When two or more hydrogen atoms are substituted, the substituents may all be the same, all may be different, or only some of them may be the same.
Substitution positions of hydrogen atoms in the aliphatic group, aryl group, heteroaryl group, arylalkyl group, alkylaryl group and trialkylsilyl group are not particularly limited. For example, when two or more hydrogen atoms are substituted, these two or more hydrogen atoms may be bonded to the same carbon atom or may be bonded to different carbon atoms.

The alkoxy group in which the hydrogen atom in R ¹ and R ² is substituted may be linear, branched or cyclic.
The alkoxy group includes, for example ^{, a} methoxy group, a cyclopropyloxy group, a monovalent monovalent groups.
The alkoxy group preferably has 1 to 6 carbon atoms.

The aryloxy group in which the hydrogen atoms in R ¹ and R ² are substituted may be either monocyclic or polycyclic.
The aryloxy group includes, for example, a phenoxy group, 1-naphthyloxy group, 2-naphthyloxy group, and the like, and a monovalent group having a structure in which the above aryl group for R ¹ and R ² is bonded to an oxygen atom. mentioned.
The aryloxy group preferably has 6 to 12 carbon atoms.

Examples of the halogen atoms with which the hydrogen atoms in R ¹ and R ² are substituted include fluorine, chlorine, bromine and iodine atoms.

In general formula (3), two R ^1s may be the same or different.
In general formula (3), two R ² may be the same or different.

In general formula (3), R ¹ is preferably a hydrogen atom, an alkyl group, an aryl group, an arylalkyl group or an alkylaryl group, and one of the alkyl groups, aryl groups, arylalkyl groups and alkylaryl groups One or more hydrogen atoms may be replaced by halogen atoms or alkoxy groups. Here, the halogen atom and the alkoxy group are the same as those described above.

When there are two or more substituted hydrogen atoms, all of the substituents may be the above-described halogen atoms, all of the above-described alkoxy groups, or both halogen atoms and alkoxy groups. may
When two or more substituents are halogen atoms, these halogen atoms may all be the same, all may be different, or only some of them may be the same. When two or more substituents are alkoxy groups, these alkoxy groups may all be the same, all may be different, or only some of them may be the same.
There are no particular restrictions on the position of the hydrogen atom substituted by the halogen atom or alkoxy group in the alkyl group, aryl group, arylalkyl group or alkylaryl group. For example, when two or more hydrogen atoms are substituted, these two or more hydrogen atoms may be bonded to the same carbon atom or may be bonded to different carbon atoms.

Among them, R ¹ is more preferably a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, a phenyl group or a benzyl group, and 1 to 3 hydrogen atoms in the phenyl group are 1 to 3 carbon atoms. may be substituted with an alkyl group, an alkoxy group, or a halogen atom.

The alkoxy substituted for the hydrogen atom in the phenyl group has 1 to 3 carbon atoms among the alkoxy groups described above. Examples of such alkoxy groups having 1 to 3 carbon atoms include methoxy, ethoxy, n-propoxy, isopropoxy and cyclopropyloxy groups.

The halogen atom with which the hydrogen atom in the phenyl group is substituted is the same as the halogen atom described above.

When the hydrogen atom in the phenyl group is substituted with the alkoxy group or halogen atom, the method of substitution is the same as the method of substitution of the hydrogen atom in the aryl group described above.

The alkyl group in which the hydrogen atom in the phenyl group is substituted has 1 to 3 carbon atoms among the linear, branched or cyclic alkyl groups for R ¹ and R ² described above. . Examples of such C 1-3 alkyl groups include methyl, ethyl, n-propyl, isopropyl and cyclopropyl groups.

When hydrogen atoms in the phenyl group are substituted with two or more of the alkyl groups, these alkyl groups may all be the same, all may be different, or only two may be the same. There may be.

The substitution position of the hydrogen atom in the phenyl group with the alkyl group, alkoxy group, or halogen atom is not particularly limited.

In general formula (3), R ² is preferably a hydrogen atom, an alkyl group, an aryl group or an alkylaryl group, and one or more hydrogen atoms in the alkyl group, aryl group or alkylaryl group may be substituted with a halogen atom or an alkoxy group.
The alkyl group, aryl group and alkylaryl group as R ² are the same as the alkyl group, aryl group and alkylaryl group as R ¹ . Halogen atoms and alkoxy groups are the same as those described above.

Among them, R ² is more preferably a hydrogen atom, an alkyl group having 1 to 5 carbon atoms or a phenyl group, and 1 to 3 hydrogen atoms in the phenyl group are alkyl groups having 1 to 3 carbon atoms. Alternatively, it may be substituted with an alkoxy group or a halogen atom.
The alkyl group having 1 to 5 carbon atoms as R ² is the same as the alkyl group having 1 to 5 carbon atoms as R ¹ .
An alkyl group having 1 to 3 carbon atoms, an alkoxy group having 1 ^{to 3 carbon atoms, and a halogen atom in which 1 to 3 hydrogen atoms in the phenyl group as R 2 are} substituted are is the same as an alkyl group having 1 to 3 carbon atoms, an alkoxy group having 1 to 3 carbon atoms, and a halogen atom in which 1 to 3 hydrogen atoms are substituted.

In general formula (3), R ³ , R ⁴ , R ⁵ and R ⁶ are each independently a hydrogen atom or a monovalent group other than a hydrogen atom (hereinafter simply abbreviated as “monovalent group”). There is).
R ³ , R ⁴ , R ⁵ and R ⁶ may all be the same, all may be different, or only some may be the same.

The monovalent groups in R ³ , R ⁴ , R ⁵ and R ⁶ may be single atoms or groups consisting of multiple atoms.
As the monovalent group for R ³ , R ⁴ , R ⁵ and R ⁶ , one or more hydrogen atoms as the above R ¹ and R ² are substituted with an alkoxy group, an aryloxy group or a halogen atom. and the same as the aliphatic group, aryl group, heteroaryl group, arylalkyl group, alkylaryl group or trialkylsilyl group that may be present. In addition to these, the monovalent groups include alkoxy groups, alkenyloxy groups, aryloxy groups, arylalkyloxy groups, alkylaryloxy groups, hydroxyl groups, halogen atoms, and the like.

The alkoxy groups for R ³ , R ⁴ , R ⁵ and R ⁶ may be linear, branched or cyclic.
The alkoxy group includes, for example, a methoxy group, a cyclopropyloxy group, and ^{the like} , and a monovalent group.
The alkoxy group preferably has 1 to 10 carbon atoms.

The alkenyloxy groups for R ³ , R ⁴ , R ⁵ and R ⁶ may be linear, branched or cyclic.
Examples of the alkenyloxy group include monovalent groups having a structure in which the alkenyl groups as the above R ¹ and R ² are bonded to an oxygen atom, such as a vinyloxy group (ethenyloxy group) and an allyloxy group. (2-propenyloxy group), cyclohexenyloxy group and the like.
The alkenyloxy group preferably has 2 to 6 carbon atoms.

The aryloxy groups for R ³ , R ⁴ , R ⁵ and R ⁶ may be either monocyclic or polycyclic.
Examples of the aryloxy group include the same aryloxy groups in which a hydrogen atom is substituted for R ¹ and R ² described above.

Examples of the arylalkyloxy group (aralkyloxy group) for R ³ , R ⁴ , R ⁵ and R ⁶ include benzyloxy group (phenylmethyloxy group), 1-phenylethyloxy group (phenethyloxy group), 2 Examples include monovalent groups having a structure in which the above arylalkyl groups as R ¹ and R ² are bonded to an oxygen atom, such as a -phenylethyloxy group.
The arylalkyloxy group preferably has 7 to 15 carbon atoms.

Examples of the alkylaryloxy group for R ³ , R ⁴ , R ⁵ and R ⁶ include 4-methylphenyloxy group, 3-methylphenyloxy group, 2-methylphenyloxy group and the like, and the above R ¹ and R A monovalent group having a structure in which the alkylaryl group for ² is bonded to an oxygen atom can be mentioned.
The arylalkyloxy group preferably has 7 to 15 carbon atoms.

Examples of the halogen atoms for R ³ , R ⁴ , R ⁵ and R ⁶ include the same halogen atoms as the above-described halogen atoms substituted for hydrogen atoms for R ¹ and R ² .

In general formula (3), R ³ , R ⁴ , R ⁵ and R ⁶ are each independently preferably a hydrogen atom, an alkyl group, an alkoxy group or a halogen atom.
The alkyl groups for R ³ , R ⁴ , R ⁵ and R ⁶ are the same as the linear, branched or cyclic alkyl groups for R ¹ and R ² described above.

Among them, R ³ , R ⁴ , R ⁵ and R ⁶ are each independently preferably a hydrogen atom, an alkyl or alkoxy group having 1 to 3 carbon atoms, or a halogen atom.
Alkyl groups having 1 to 3 carbon atoms, alkoxy groups having 1 to 3 carbon atoms, and halogen atoms as R ³ , R ⁴ , R ⁵ and R ⁶ are 1 to 3 hydrogen atoms in the phenyl group as R ¹ It is the same as an alkyl group having 1 to 3 carbon atoms, an alkoxy group having 1 to 3 carbon atoms, and a halogen atom on which atoms are substituted.

In general formula (3), two R ³ may be the same or different.
In general formula (3), two R ^4s may be the same or different.
In general formula (3), two R ^5s may be the same or different.
In general formula (3), two R ⁶ may be the same or different.

In general formula (3), ^R7 and ^R8 each independently represent a hydrogen atom, a halogen atom, an aliphatic group, an aryl group, an alkoxy group, an aryloxy group, a heteroaryl group, an arylalkyl group, an alkylaryl group, or It is a trialkylsilyl group.
R ⁷ and R ⁸ may be the same or different.

The aliphatic group, aryl group, heteroaryl group, arylalkyl group, alkylaryl group and trialkylsilyl group for R ⁷ and R ⁸ are the above-mentioned aliphatic groups, aryl groups and heteroaryl groups for R ¹ and R ² . The same applies to aryl groups, arylalkyl groups, alkylaryl groups and trialkylsilyl groups.
For example, ^the aliphatic group for R ⁷ and R ⁸ may be either a saturated aliphatic group or an unsaturated aliphatic group, and the unsaturated aliphatic group ^includes It is the same as the unsaturated aliphatic group. In the unsaturated aliphatic group as R ⁷ or R ⁸ , a carbon atom bonded to a carbon atom constituting a bicyclo ring skeleton (a ring skeleton derived from compound (2) described later), and this carbon atom It is preferable that the bond between the carbon atom adjacent to and is not an unsaturated bond, and the number of unsaturated bonds is preferably as small as possible.

The halogen atoms in R ⁷ and R ⁸ are the same as the halogen atoms in which the hydrogen atoms in R ¹ and R ² described above are substituted.
The alkoxy group and aryloxy group for R ⁷ and R ⁸ are the same as the alkoxy group and aryloxy group in which a hydrogen atom is substituted for R ¹ and R ² described above.

Among R ⁷ and R ⁸ , the aliphatic group, alkoxy group, aryloxy group, arylalkyl group, alkylaryl group or trialkylsilyl group is one or two or more methylene groups (-CH ₂ -), the methylene group is an oxygen atom (-O-), a sulfur atom (-S-), a carbonyloxy group (-C (=O) -O-) or an oxycarbonyl group (-O- C(=O)-) may be substituted.
In R ⁷ and R ⁸ , the number of methylene groups substituted with these substituents is preferably 1 to 3, more preferably 1 or 2.

1 or 2 or more hydrogen atoms in the aliphatic group, aryl group, alkoxy group, aryloxy group, heteroaryl group, arylalkyl group, alkylaryl group or trialkylsilyl group among R ⁷ and R ⁸ may be substituted with an alkyl group, an aryl group, an alkoxy group, an aryloxy group or a halogen atom.
Examples of the alkyl group and aryl group in which the hydrogen atom is substituted include the same alkyl group and aryl group as those described above for R ¹ and R ² .
Examples of the alkoxy group, aryloxy group and halogen atom with which the hydrogen atom is substituted include the same alkoxy group, aryloxy group and halogen atom with which the hydrogen atom is substituted in R ¹ and R ² described above.
In R ⁷ and R ⁸ , the number of hydrogen atoms substituted by these substituents is preferably 1 to 3, more preferably 1 or 2.

In general formula (3), R ⁹ is a hydrogen atom, a halogen atom, an aliphatic group, an aryl group, an alkoxy group, an aryloxy group, a heteroaryl group, an arylalkyl group, an alkylaryl group, a trialkylsilyl group, or a phthalimidoyl is the base.
The aliphatic group, aryl group, heteroaryl group, arylalkyl group, alkylaryl group and trialkylsilyl group for R ⁹ are the same as the above-described aliphatic group, aryl group, heteroaryl group for R ¹ and R ² , It is the same as the arylalkyl group, alkylaryl group and trialkylsilyl group.
The halogen atom for R ⁹ is the same as the halogen atom with which the hydrogen atom for R ¹ and R ² described above is substituted.
The alkoxy group and aryloxy group for R ⁹ are the same as the alkoxy group and aryloxy group in which the hydrogen atom is substituted for R ¹ and R ² described above.

Among R ⁹ , one or two or more methylene groups (-CH ₂ -) which are not adjacent to each other are said aliphatic group, alkoxy group, aryloxy group, arylalkyl group, alkylaryl group or trialkylsilyl group. , the methylene group is an oxygen atom (-O-), a sulfur atom (-S-), a carbonyloxy group (-C(=O)-O-) or an oxycarbonyl group (-O-C(= O)-) may be substituted.
In R ⁹ , the number of methylene groups substituted with these substituents is preferably 1 to 3, more preferably 1 or 2.

One or more hydrogen atoms in the aliphatic group, aryl group, alkoxy group, aryloxy group, heteroaryl group, arylalkyl group, alkylaryl group or trialkylsilyl group in ^R9 are alkyl groups, aryl groups, alkoxy groups, aryloxy groups or halogen atoms.
Examples of the alkyl group and aryl group in which the hydrogen atom is substituted include the same alkyl group and aryl group as those described above for R ¹ and R ² .
Examples of the alkoxy group, aryloxy group and halogen atom with which the hydrogen atom is substituted include the same alkoxy group, aryloxy group and halogen atom with which the hydrogen atom is substituted in R ¹ and R ² described above.
In R ⁹ , the number of hydrogen atoms substituted with these substituents is preferably 1 to 3, more preferably 1 or 2.

In general formula (3), R ⁷ , R ⁸ and R ⁹ are each independently a hydrogen atom, a halogen atom, an alkyl group, an aryl group, an alkoxy group, an aryloxy group, an arylalkyl group or an alkylaryl group. is preferred.
Among them, R ⁷ , R ⁸ and R ⁹ are more preferably each independently a hydrogen atom, a halogen atom, an alkyl or alkoxy group having 1 to 5 carbon atoms, a phenyl group, a phenoxy group or a benzyl group. , R ⁷ , R ⁸ and R ⁹ , 1 to 3 hydrogen atoms in the phenyl groups may be substituted with an alkyl group or alkoxy group having 1 to 3 carbon atoms or a halogen atom.

In general formula (3), when two or more of R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁶ bonded to the same ring skeleton are organic groups, these two The above organic groups may be bonded together to form a ring together with the ring skeleton to which these organic groups are bonded.
Here, "the same ring skeleton" means either one of two indole ring skeletons, and the ring may be formed by only one of the two indole ring skeletons, Both may form the ring.
Further, the “organic group” is the above-described aliphatic group, aryl group, heteroaryl group, arylalkyl group, alkylaryl group or trialkylsilyl group for R ¹ and R ² , and R ³ and R ⁴ , R ⁵ and R ⁶ correspond to organic groups among the above monovalent groups other than hydrogen atoms.

The ring formed by two or more of R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁶ may be either monocyclic or polycyclic.
The number of ring members (the number of atoms forming the ring skeleton) of the ring thus formed is not particularly limited, but is preferably 4-10.

In general formula (3), when two or more of R ⁷ , R ⁸ and R ⁹ are organic groups, these two or more organic groups are bonded to each other, and these organic groups are bonded to may form a ring together with the existing ring skeleton.
Here, the “organic group” means the above-mentioned aliphatic group, aryl group, alkoxy group, aryloxy group, heteroaryl group, arylalkyl group, alkylaryl group or trialkylsilyl group for R ⁷ and R ⁸ and R ⁹ is the aforementioned aliphatic group, aryl group, alkoxy group, aryloxy group, heteroaryl group, arylalkyl group, alkylaryl group, trialkylsilyl group or phthalimidoyl group.

The ring formed by two or more of R ⁷ , R ⁸ and R ⁹ may be either monocyclic or polycyclic.
The number of ring members (the number of atoms forming the ring skeleton) of the ring thus formed is not particularly limited, but is preferably 4-10.

Preferred compounds (3) include, for example, any combination of the above preferred R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ and R ⁹ mentioned.

More preferred compounds (3) include, for example, R ¹ is a hydrogen atom, an alkyl group, an aryl group, an arylalkyl group or an alkylaryl group, and the alkyl group, aryl group, arylalkyl group or alkylaryl group One or more hydrogen atoms may be substituted with a halogen atom or an alkoxy group, R ² is a hydrogen atom, an alkyl group, an aryl group or an alkylaryl group, and the alkyl group, aryl group or One or more hydrogen atoms in the alkylaryl group may be substituted with a halogen atom or an alkoxy group, and R ³ , R ⁴ , R ⁵ and R ⁶ each independently represent a hydrogen atom, an alkyl groups, alkoxy groups or halogen atoms. Furthermore, in such compound (3), R ⁷ , R ⁸ and R ⁹ are each independently a hydrogen atom, a halogen atom, an alkyl group, an aryl group, an alkoxy group, an aryloxy group, an arylalkyl group or an alkyl An aryl group is preferred.

More preferred compounds (3) include, for example, R ¹ being a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, a phenyl group or a benzyl group, and 1 to 3 hydrogen atoms in the phenyl group as R ¹ The atom may be substituted with an alkyl group or alkoxy group having 1 to 3 carbon atoms or a halogen atom, R ² is a ^hydrogen atom, an alkyl group having 1 to 5 carbon atoms or a phenyl group, and 1 to 3 hydrogen atoms in the phenyl group may be substituted with an alkyl group or alkoxy group having 1 to 3 carbon atoms or a halogen atom, and R ³ , R ⁴ , R ⁵ and R ⁶ are each Independently, those which are a hydrogen atom, an alkyl group or an alkoxy group having 1 to 3 carbon atoms, or a halogen atom are included. Further, in such compound (3), R ⁷ , R ⁸ and R ⁹ are each independently a hydrogen atom, a halogen atom, an alkyl or alkoxy group having 1 to 5 carbon atoms, a phenyl group, a phenoxy group or A benzyl group is preferable, and 1 to 3 hydrogen atoms in the phenyl group as R ⁷ , R ⁸ and R ⁹ are substituted with an alkyl group having 1 to 3 carbon atoms, an alkoxy group, or a halogen atom. may

In general formula (3), two indole ring skeletons may be the same or different. That is, in the two indole ring skeletons in the compound (3), all combinations of R ¹ , R ² , R ³ , R ⁴ , R ⁵ , and R ⁶ are the same. Alternatively, all combinations may be different, or only some combinations (that is, combinations of any one to five) may be different.
In general formula (3), the two indole ring skeletons are preferably the same from the viewpoint that the desired product can be obtained more easily and in a higher yield.

Preferred compounds (3) in which R ¹ to R ⁹ are defined as described above are shown below as represented by the general formula (301).

（式中、Ｒ^１１は、水素原子、炭素数１～５のアルキル基、フェニル基又はベンジル基であり、前記フェニル基中の１～３個の水素原子は、炭素数１～３のアルキル基若しくはアルコキシ基又はハロゲン原子で置換されていてもよく；
Ｒ^２１は、水素原子、炭素数１～５のアルキル基又はフェニル基であり、前記フェニル基中の１～３個の水素原子は、炭素数１～３のアルキル基若しくはアルコキシ基又はハロゲン原子で置換されていてもよく；
Ｒ^３１、Ｒ^４１、Ｒ^５１及びＲ^６１は、それぞれ独立に、水素原子、炭素数１～３のアルキル基若しくはアルコキシ基又はハロゲン原子であり；
Ｒ^７１、Ｒ^８１及びＲ^９１は、それぞれ独立に、水素原子、ハロゲン原子、炭素数１～５のアルキル基若しくはアルコキシ基、フェニル基、フェノキシ基又はベンジル基であり、前記フェニル基中の１～３個の水素原子は、炭素数１～３のアルキル基若しくはアルコキシ基又はハロゲン原子で置換されていてもよく；
同一の環骨格に結合している、Ｒ^１１、Ｒ^２１、Ｒ^３１、Ｒ^４１、Ｒ^５１及びＲ^６１のうち、２個以上が有機基である場合、これら２個以上の有機基は、相互に結合して環を形成していてもよく；
Ｒ^７１、Ｒ^８１及びＲ^９１のうち、２個以上が有機基である場合、これら２個以上の有機基は、相互に結合して環を形成していてもよい。）

(In the formula, R ¹¹ is a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, a phenyl group or a benzyl group, and 1 to 3 hydrogen atoms in the phenyl group are alkyl groups having 1 to 3 carbon atoms. or may be substituted with an alkoxy group or a halogen atom;
R ²¹ is a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, or a phenyl group, and 1 to 3 hydrogen atoms in the phenyl group are an alkyl group having 1 to 3 carbon atoms, an alkoxy group, or a halogen atom; optionally substituted;
R ³¹ , R ⁴¹ , R ⁵¹ and R ⁶¹ are each independently a hydrogen atom, an alkyl or alkoxy group having 1 to 3 carbon atoms, or a halogen atom;
R ⁷¹ , R ⁸¹ and R ⁹¹ are each independently a hydrogen atom, a halogen atom, an alkyl or alkoxy group having 1 to 5 carbon atoms, a phenyl group, a phenoxy group or a benzyl group, and 1 to 3 hydrogen atoms may be substituted with an alkyl or alkoxy group having 1 to 3 carbon atoms or a halogen atom;
When two or more of R ¹¹ , R ²¹ , R ³¹ , R ⁴¹ , R ⁵¹ and R ⁶¹ bonded to the same ring skeleton are organic groups, these two or more organic groups are may be linked to form a ring;
When two or more of R ⁷¹ , R ⁸¹ and R ⁹¹ are organic groups, these two or more organic groups may combine with each other to form a ring. )

Here, the “organic group” for R ¹¹ is the above-mentioned alkyl group having 1 to 5 carbon atoms, benzyl group, or phenyl group which may have a substituent, and for R ²¹ , the above-mentioned or an optionally substituted phenyl group, and R ³¹ , R ⁴¹ , R ⁵¹ and R ⁶¹ are the above-mentioned C 1-3 alkyl groups or an alkoxy group, and R ⁷¹ , R ⁸¹ and R ⁹¹ are the above-described alkyl group or alkoxy group having 1 to 5 carbon atoms, phenoxy group, benzyl group, or a phenyl group which may have a substituent; .

<<Compound (3a)>>
A compound according to one embodiment of the present invention (in this specification, may be referred to as "compound (3a)") is represented by the following general formula (3a).

（式中、Ｒ^１及びＲ^２は、それぞれ独立に、水素原子、脂肪族基、アリール基、ヘテロアリール基、アリールアルキル基、アルキルアリール基又はトリアルキルシリル基であり、前記脂肪族基、アリール基、ヘテロアリール基、アリールアルキル基、アルキルアリール基又はトリアルキルシリル基中の１個又は２個以上の水素原子は、アルコキシ基、アリールオキシ基又はハロゲン原子で置換されていてもよく；
Ｒ^３、Ｒ^４、Ｒ^５及びＲ^６は、それぞれ独立に、水素原子又は水素原子以外の一価の基であり；
Ｒ^７及びＲ^８は、それぞれ独立に、水素原子、ハロゲン原子、脂肪族基、アリール基、アルコキシ基、アリールオキシ基、ヘテロアリール基、アリールアルキル基、アルキルアリール基又はトリアルキルシリル基であり、前記脂肪族基、アルコキシ基、アリールオキシ基、アリールアルキル基、アルキルアリール基又はトリアルキルシリル基が１個又は互いに隣接していない２個以上のメチレン基を有する場合、前記メチレン基は、酸素原子、硫黄原子、カルボニルオキシ基又はオキシカルボニル基で置換されていてもよく、前記脂肪族基、アリール基、アルコキシ基、アリールオキシ基、ヘテロアリール基、アリールアルキル基、アルキルアリール基又はトリアルキルシリル基中の１個又は２個以上の水素原子は、アルキル基、アリール基、アルコキシ基、アリールオキシ基又はハロゲン原子で置換されていてもよく；
Ｒ^９は、水素原子、ハロゲン原子、脂肪族基、アリール基、アルコキシ基、アリールオキシ基、ヘテロアリール基、アリールアルキル基、アルキルアリール基、トリアルキルシリル基又はフタルイミドイル基であり、前記脂肪族基、アルコキシ基、アリールオキシ基、アリールアルキル基、アルキルアリール基又はトリアルキルシリル基が１個又は互いに隣接していない２個以上のメチレン基を有する場合、前記メチレン基は、酸素原子、硫黄原子、カルボニルオキシ基又はオキシカルボニル基で置換されていてもよく、前記脂肪族基、アリール基、アルコキシ基、アリールオキシ基、ヘテロアリール基、アリールアルキル基、アルキルアリール基又はトリアルキルシリル基中の１個又は２個以上の水素原子は、アルキル基、アリール基、アルコキシ基、アリールオキシ基又はハロゲン原子で置換されていてもよく；
２個のＲ^１、Ｒ^２、Ｒ^３、Ｒ^４、Ｒ^５及びＲ^６は、それぞれ互いに同一でも異なっていてもよく；
同一の環骨格に結合している、Ｒ^１、Ｒ^２、Ｒ^３、Ｒ^４、Ｒ^５及びＲ^６のうち、２個以上が有機基である場合、これら２個以上の有機基は、相互に結合して環を形成していてもよく；
Ｒ^７、Ｒ^８及びＲ^９のうち、２個以上が有機基である場合、これら２個以上の有機基は、相互に結合して環を形成していてもよい。）

(wherein R ¹ and R ² are each independently a hydrogen atom, an aliphatic group, an aryl group, a heteroaryl group, an arylalkyl group, an alkylaryl group or a trialkylsilyl group; one or more hydrogen atoms in the group, heteroaryl group, arylalkyl group, alkylaryl group or trialkylsilyl group may be replaced by an alkoxy group, an aryloxy group or a halogen atom;
R ³ , R ⁴ , R ⁵ and R ⁶ are each independently a hydrogen atom or a monovalent group other than a hydrogen atom;
^R7 and ^R8 are each independently a hydrogen atom, a halogen atom, an aliphatic group, an aryl group, an alkoxy group, an aryloxy group, a heteroaryl group, an arylalkyl group, an alkylaryl group or a trialkylsilyl group; When the aliphatic group, alkoxy group, aryloxy group, arylalkyl group, alkylaryl group or trialkylsilyl group has one or two or more methylene groups that are not adjacent to each other, the methylene group is an oxygen atom. , a sulfur atom, a carbonyloxy group or an oxycarbonyl group, the aliphatic group, aryl group, alkoxy group, aryloxy group, heteroaryl group, arylalkyl group, alkylaryl group or trialkylsilyl group one or more hydrogen atoms in may be substituted with an alkyl group, an aryl group, an alkoxy group, an aryloxy group or a halogen atom;
^R9 is a hydrogen atom, a halogen atom, an aliphatic group, an aryl group, an alkoxy group, an aryloxy group, a heteroaryl group, an arylalkyl group, an alkylaryl group, a trialkylsilyl group or a phthalimidoyl group, and the aliphatic When the group, alkoxy group, aryloxy group, arylalkyl group, alkylaryl group or trialkylsilyl group has one or two or more non-adjacent methylene groups, the methylene groups are oxygen atoms, sulfur atoms , a carbonyloxy group or an oxycarbonyl group, and one of the aliphatic groups, aryl groups, alkoxy groups, aryloxy groups, heteroaryl groups, arylalkyl groups, alkylaryl groups and trialkylsilyl groups one or more hydrogen atoms may be replaced by an alkyl group, an aryl group, an alkoxy group, an aryloxy group or a halogen atom;
two R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁶ may be the same or different;
When two or more of R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁶ bonded to the same ring skeleton are organic groups, these two or more organic groups are may be linked to form a ring;
When two or more of R ⁷ , R ⁸ and R ⁹ are organic groups, these two or more organic groups may combine with each other to form a ring. )

Compound (3a) is a synthetic intermediate of compound (3) and can be stably isolated. A method for producing compound (3) via compound (3a) will be described later in detail.

In general formula (3a), R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ and R ⁹ are R ¹ , R ² and R ³ in general formula (3) , R ⁴ , R ⁵ , R ⁶ , R ^{7 ,} R ⁸ and R ⁹ .

Compound (3a) has multiple stereoisomers, and all stereoisomers are included in this embodiment.

Preferred compounds (3a) include those of R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ and R ⁹ corresponding to those previously mentioned as preferred compounds (3). Combinations are included.

For example, a more preferable compound (3a) is one in which R ¹ is a hydrogen atom, an alkyl group, an aryl group, an arylalkyl group or an alkylaryl group, and the alkyl group, aryl group, arylalkyl group or alkylaryl group One or more hydrogen atoms may be substituted with a halogen atom or an alkoxy group, R ² is a hydrogen atom, an alkyl group, an aryl group or an alkylaryl group, and the alkyl group, aryl group or One or more hydrogen atoms in the alkylaryl group may be substituted with a halogen atom or an alkoxy group, and R ³ , R ⁴ , R ⁵ and R ⁶ each independently represent a hydrogen atom, an alkyl groups, alkoxy groups or halogen atoms. Furthermore, in such compound (3a), R ⁷ , R ⁸ and R ⁹ are each independently a hydrogen atom, a halogen atom, an alkyl group, an aryl group, an alkoxy group, an aryloxy group, an arylalkyl group or an alkyl An aryl group is preferred.

More preferred compounds (3a) include, for example, R ¹ being a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, a phenyl group or a benzyl group, and 1 to 3 hydrogen atoms in the phenyl group as R ¹ The atom may be substituted with an alkyl group or alkoxy group having 1 to 3 carbon atoms or a halogen atom, R ² is a ^hydrogen atom, an alkyl group having 1 to 5 carbon atoms or a phenyl group, and 1 to 3 hydrogen atoms in the phenyl group may be substituted with an alkyl group or alkoxy group having 1 to 3 carbon atoms or a halogen atom, and R ³ , R ⁴ , R ⁵ and R ⁶ are each Independently, those which are a hydrogen atom, an alkyl group or an alkoxy group having 1 to 3 carbon atoms, or a halogen atom are included. Further, in such compound (3a), R ⁷ , R ⁸ and R ⁹ are each independently a hydrogen atom, a halogen atom, an alkyl or alkoxy group having 1 to 5 carbon atoms, a phenyl group, a phenoxy group or A benzyl group is preferable, and 1 to 3 hydrogen atoms in the phenyl group as R ⁷ , R ⁸ and R ⁹ are substituted with an alkyl group having 1 to 3 carbon atoms, an alkoxy group, or a halogen atom. may

In general formula (3a), two indole ring skeletons may be the same or different. That is, in the two indole ring skeletons in compound (3a), all combinations of R ¹ , R ² , R ³ , R ⁴ , R ⁵ , and R ⁶ are the same. Alternatively, all combinations may be different, or only some combinations (that is, combinations of any one to five) may be different.
In general formula (3a), the two indole ring skeletons are preferably the same from the viewpoint that the desired product can be obtained more easily and in a higher yield.

Preferred compounds (3a) in which R ¹ to R ⁹ are defined as described above are shown below as represented by general formula (301a).

（式中、Ｒ^１１は、水素原子、炭素数１～５のアルキル基、フェニル基又はベンジル基であり、前記フェニル基中の１～３個の水素原子は、炭素数１～３のアルキル基若しくはアルコキシ基又はハロゲン原子で置換されていてもよく；
Ｒ^２１は、水素原子、炭素数１～５のアルキル基又はフェニル基であり、前記フェニル基中の１～３個の水素原子は、炭素数１～３のアルキル基若しくはアルコキシ基又はハロゲン原子で置換されていてもよく；
Ｒ^３１、Ｒ^４１、Ｒ^５１及びＲ^６１は、それぞれ独立に、水素原子、炭素数１～３のアルキル基若しくはアルコキシ基又はハロゲン原子であり；
Ｒ^７１、Ｒ^８１及びＲ^９１は、それぞれ独立に、水素原子、ハロゲン原子、炭素数１～５のアルキル基若しくはアルコキシ基、フェニル基、フェノキシ基又はベンジル基であり、前記フェニル基中の１～３個の水素原子は、炭素数１～３のアルキル基若しくはアルコキシ基又はハロゲン原子で置換されていてもよく；
同一の環骨格に結合している、Ｒ^１１、Ｒ^２１、Ｒ^３１、Ｒ^４１、Ｒ^５１及びＲ^６１のうち、２個以上が有機基である場合、これら２個以上の有機基は、相互に結合して環を形成していてもよく；
Ｒ^７１、Ｒ^８１及びＲ^９１のうち、２個以上が有機基である場合、これら２個以上の有機基は、相互に結合して環を形成していてもよい。）

(In the formula, R ¹¹ is a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, a phenyl group or a benzyl group, and 1 to 3 hydrogen atoms in the phenyl group are alkyl groups having 1 to 3 carbon atoms. or may be substituted with an alkoxy group or a halogen atom;
R ²¹ is a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, or a phenyl group, and 1 to 3 hydrogen atoms in the phenyl group are an alkyl group having 1 to 3 carbon atoms, an alkoxy group, or a halogen atom; optionally substituted;
R ³¹ , R ⁴¹ , R ⁵¹ and R ⁶¹ are each independently a hydrogen atom, an alkyl or alkoxy group having 1 to 3 carbon atoms, or a halogen atom;
R ⁷¹ , R ⁸¹ and R ⁹¹ are each independently a hydrogen atom, a halogen atom, an alkyl or alkoxy group having 1 to 5 carbon atoms, a phenyl group, a phenoxy group or a benzyl group, and 1 to 3 hydrogen atoms may be substituted with an alkyl or alkoxy group having 1 to 3 carbon atoms or a halogen atom;
When two or more of R ¹¹ , R ²¹ , R ³¹ , R ⁴¹ , R ⁵¹ and R ⁶¹ bonded to the same ring skeleton are organic groups, these two or more organic groups are may be linked to form a ring;
When two or more of R ⁷¹ , R ⁸¹ and R ⁹¹ are organic groups, these two or more organic groups may combine with each other to form a ring. )

<<Method for producing compound (3) and compound (3a)>>
Compound (3) is a compound represented by the following general formula (1) (in this specification, sometimes referred to as "compound (1)") and a compound represented by the following general formula (2) ( In this specification, it may be referred to as "compound (2)") in the presence of an acid catalyst to obtain compound (3).

（式中、Ｒ^１及びＲ^２は、それぞれ独立に、水素原子、脂肪族基、アリール基、ヘテロアリール基、アリールアルキル基、アルキルアリール基又はトリアルキルシリル基であり、前記脂肪族基、アリール基、ヘテロアリール基、アリールアルキル基、アルキルアリール基又はトリアルキルシリル基中の１個又は２個以上の水素原子は、アルコキシ基、アリールオキシ基又はハロゲン原子で置換されていてもよく；
Ｒ^３、Ｒ^４、Ｒ^５及びＲ^６は、それぞれ独立に、水素原子又は水素原子以外の一価の基であり；
Ｒ^７及びＲ^８は、それぞれ独立に、水素原子、ハロゲン原子、脂肪族基、アリール基、アルコキシ基、アリールオキシ基、ヘテロアリール基、アリールアルキル基、アルキルアリール基又はトリアルキルシリル基であり、前記脂肪族基、アルコキシ基、アリールオキシ基、アリールアルキル基、アルキルアリール基又はトリアルキルシリル基が１個又は互いに隣接していない２個以上のメチレン基を有する場合、前記メチレン基は、酸素原子、硫黄原子、カルボニルオキシ基又はオキシカルボニル基で置換されていてもよく、前記脂肪族基、アリール基、アルコキシ基、アリールオキシ基、ヘテロアリール基、アリールアルキル基、アルキルアリール基又はトリアルキルシリル基中の１個又は２個以上の水素原子は、アルキル基、アリール基、アルコキシ基、アリールオキシ基又はハロゲン原子で置換されていてもよく；
Ｒ^９は、水素原子、ハロゲン原子、脂肪族基、アリール基、アルコキシ基、アリールオキシ基、ヘテロアリール基、アリールアルキル基、アルキルアリール基、トリアルキルシリル基又はフタルイミドイル基であり、前記脂肪族基、アルコキシ基、アリールオキシ基、アリールアルキル基、アルキルアリール基又はトリアルキルシリル基が１個又は互いに隣接していない２個以上のメチレン基を有する場合、前記メチレン基は、酸素原子、硫黄原子、カルボニルオキシ基又はオキシカルボニル基で置換されていてもよく、前記脂肪族基、アリール基、アルコキシ基、アリールオキシ基、ヘテロアリール基、アリールアルキル基、アルキルアリール基又はトリアルキルシリル基中の１個又は２個以上の水素原子は、アルキル基、アリール基、アルコキシ基、アリールオキシ基又はハロゲン原子で置換されていてもよく；
２個のＲ^１、Ｒ^２、Ｒ^３、Ｒ^４、Ｒ^５及びＲ^６は、それぞれ互いに同一でも異なっていてもよく；
同一の環骨格に結合している、Ｒ^１、Ｒ^２、Ｒ^３、Ｒ^４、Ｒ^５及びＲ^６のうち、２個以上が有機基である場合、これら２個以上の有機基は、相互に結合して環を形成していてもよく；
Ｒ^７、Ｒ^８及びＲ^９のうち、２個以上が有機基である場合、これら２個以上の有機基は、相互に結合して環を形成していてもよい。）

(wherein R ¹ and R ² are each independently a hydrogen atom, an aliphatic group, an aryl group, a heteroaryl group, an arylalkyl group, an alkylaryl group or a trialkylsilyl group; one or more hydrogen atoms in the group, heteroaryl group, arylalkyl group, alkylaryl group or trialkylsilyl group may be replaced by an alkoxy group, an aryloxy group or a halogen atom;
R ³ , R ⁴ , R ⁵ and R ⁶ are each independently a hydrogen atom or a monovalent group other than a hydrogen atom;
^R7 and ^R8 are each independently a hydrogen atom, a halogen atom, an aliphatic group, an aryl group, an alkoxy group, an aryloxy group, a heteroaryl group, an arylalkyl group, an alkylaryl group or a trialkylsilyl group; When the aliphatic group, alkoxy group, aryloxy group, arylalkyl group, alkylaryl group or trialkylsilyl group has one or two or more methylene groups that are not adjacent to each other, the methylene group is an oxygen atom. , a sulfur atom, a carbonyloxy group or an oxycarbonyl group, the aliphatic group, aryl group, alkoxy group, aryloxy group, heteroaryl group, arylalkyl group, alkylaryl group or trialkylsilyl group one or more hydrogen atoms in may be substituted with an alkyl group, an aryl group, an alkoxy group, an aryloxy group or a halogen atom;
^R9 is a hydrogen atom, a halogen atom, an aliphatic group, an aryl group, an alkoxy group, an aryloxy group, a heteroaryl group, an arylalkyl group, an alkylaryl group, a trialkylsilyl group or a phthalimidoyl group, and the aliphatic When the group, alkoxy group, aryloxy group, arylalkyl group, alkylaryl group or trialkylsilyl group has one or two or more non-adjacent methylene groups, the methylene groups are oxygen atoms, sulfur atoms , a carbonyloxy group or an oxycarbonyl group, and one of the aliphatic groups, aryl groups, alkoxy groups, aryloxy groups, heteroaryl groups, arylalkyl groups, alkylaryl groups and trialkylsilyl groups one or more hydrogen atoms may be replaced by an alkyl group, an aryl group, an alkoxy group, an aryloxy group or a halogen atom;
two R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁶ may be the same or different;
When two or more of R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁶ bonded to the same ring skeleton are organic groups, these two or more organic groups are may be linked to form a ring;
When two or more of R ⁷ , R ⁸ and R ⁹ are organic groups, these two or more organic groups may combine with each other to form a ring. )

<Compound (1)>
Compound (1) is indole or a derivative thereof, and is one starting material for compound (3).
R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁶ in general formula (1) correspond to R ¹ , R ² , R 3 , R ⁴ , R ⁵ and ^{R 6 in} general formula (3) is the same as

Preferred compounds (1) include those having combinations of R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁶ corresponding to those listed above for preferred compounds (3).

The compound (1) subjected to the reaction may be of one type or two or more types, and may be appropriately selected according to the structure of the target compound (3).
When two or more compounds (1) are used, their combination and ratio can be appropriately adjusted according to the purpose.
For example, when producing compound (3) in which two indole ring skeletons in general formula (3) (in other words, in one molecule) are the same as described above, compound (1) is It is preferred to use seeds only.
On the other hand, when producing compound (3) in which two indole ring skeletons in one molecule are different from each other, it is necessary to use at least two types of compound (1), and three or more types may be used.
For example, when one type of compound (2) and two or more types of compounds (1) are used, one or more compounds (3) having two different indole ring skeletons in one molecule Two or more types may be produced, and in addition to these, one or two or more types of compound (3) having two identical indole ring skeletons in one molecule may be produced. As described above, when two or more compounds (1) are used, various compounds (3) may be produced. However, by adjusting the reaction conditions, the target compound (3) Improved production may be possible.

In this specification, stereoisomers are not taken into account in the description of the number of types of compound (3) as described above, unless otherwise specified.

The amount of compound (1) used can be appropriately adjusted according to the type of compound (2), the target yield of compound (3), and the like.
The amount of compound (1) used may be, for example, either 0.5 to 6 times the molar amount of compound (2) or 1 to 6 times the molar amount, but it should be 2 to 6 times the molar amount. is preferred, 2- to 5-fold molar amount is more preferred, and 2- to 4-fold molar amount is even more preferred. When the amount of compound (1) used is at least twice the molar amount of compound (2), the yield of compound (3) is further improved. On the other hand, excessive use of compound (1) is suppressed because the amount of compound (1) to be used is equal to or less than the upper limit.

<Compound (2)>
Compound (2) is the other raw material for compound (3).
In general formula (2), ^R7 , ^R8 and ^R9 are the same as ^R7 , ^R8 and ^R9 in general formula (3).

Preferred compounds (2) include those having combinations of R ⁷ , R ⁸ and R ⁹ corresponding to those listed above for preferred compounds (3).

The compound (2) to be subjected to the reaction may be of one type or two or more types, but usually preferably of only one type.
When two or more compounds (2) are used, their combination and ratio can be appropriately adjusted depending on the purpose.
For example, when two or more types of compounds (2) and one type of compound (1) are used, compound (3) in which two indole ring skeletons in one molecule are identical to each other is one There is a possibility that a species or two or more species are produced, and it may be possible to improve the production amount of the desired compound (3) by adjusting the reaction conditions.

<Acid catalyst>
The acid catalyst can promote the reaction between compound (1) and compound (2).
The acid catalyst may be, for example, either Bronsted acid or Lewis acid.

[Bronsted acid]
The Bronsted acid may be a known one.
Preferred Bronsted acids include, for example, sulfonic acid having no fluorine atom (in this specification, may be referred to as "fluorine-free sulfonic acid"), proton (H ⁺ ) donor having fluorine atom ( In the present specification, it may be referred to as a "fluorine-containing Bronsted acid") and the like.

Examples of the fluorine-free sulfonic acid include methanesulfonic acid (CH ₃ SO ₃ H, sometimes referred to as “MsOH”), benzenesulfonic acid (C ₆ H ₅ SO ₃ H), p-toluenesulfonic acid ( p-CH ₃ C ₆ H ₄ SO ₃ H, sometimes referred to as “p-TsOH” in this specification) and the like. The p-toluenesulfonic acid may be a monohydrate (which may be abbreviated as "p-TsOH.H ₂ O" herein).

The fluorine-containing Bronsted acid is not particularly limited as long as it has a fluorine atom in its structure.
The fluorine-containing Bronsted acid may be, for example, either a fluorine-containing inorganic acid or a fluorine-containing organic acid.

Examples of fluorine-containing inorganic acids include tetrafluoroboric acid (HBF ₄ ).
Tetrafluoroboric acid can be used, for example, as its aqueous solution (HBF ₄ aq.).

Examples of fluorine-containing organic acids include those having a fluorine-containing electron-withdrawing group (an electron-withdrawing group having a fluorine atom).
Preferred fluorine-containing electron-withdrawing groups include, for example, fluoroalkyl groups, fluoroalkylene groups, fluoroaryl groups, and fluoroarylene groups.

The fluoroalkyl group and fluoroalkylene group may be linear, branched or cyclic, but are preferably linear or branched.
The fluoroaryl group and fluoroarylene group may be either monocyclic or polycyclic, but are preferably monocyclic.

The number of fluorine atoms possessed by the fluoroalkyl group, fluoroalkylene group, fluoroaryl group and fluoroarylene group is not particularly limited, but the number of hydrogen atoms possessed by these groups is preferably as small as possible. (in other words, all hydrogen atoms are replaced with fluorine atoms).
Specifically, the fluoroalkyl group, fluoroalkylene group, fluoroaryl group and fluoroarylene group are particularly preferably perfluoroalkyl groups, perfluoroalkylene groups, perfluoroaryl groups and perfluoroarylene groups, respectively.

One molecule of the fluorine-containing organic acid may have only one fluorine-containing electron-withdrawing group selected from the group consisting of a fluoroalkyl group, a fluoroalkylene group, a fluoroaryl group and a fluoroarylene group. , may have two or more. When one molecule of a fluorine-containing organic acid has two or more fluorine-containing electron-withdrawing groups, these two or more fluorine-containing electron-withdrawing groups may be the same or different. may be the same, or may be partially the same. A part or all of these two or more fluorine-containing electron-withdrawing groups may be bonded together to form a ring together with the sites to which these fluorine-containing electron-withdrawing groups are bonded. good.
The fluorine-containing organic acid preferably has one or both of a fluoroalkyl group and a fluoroalkylene group as essential fluorine-containing electron-withdrawing groups.

The fluorine-containing organic acid has one or more fluorine-containing electron-withdrawing groups selected from the group consisting of fluoroalkylsulfonyl groups, fluoroalkylenesulfonyl groups, fluoroarylsulfonyl groups and fluoroarylenesulfonyl groups. more preferred. For example, a fluorine-containing organic acid having a fluoroalkylsulfonyl group corresponds to the above fluorine-containing organic acid having a fluoroalkyl group.
In the fluorine-containing organic acid, the fluoroalkylsulfonyl group, fluoroalkylenesulfonyl group, fluoroarylsulfonyl group and fluoroarylenesulfonyl group are preferably directly bonded to the atom to which the hydrogen atom donated as a proton is bonded. .

In the fluorine-containing organic acid, the atom to which the hydrogen atom donated as a proton is bonded is divalent or higher, preferably trivalent or higher, more preferably a nitrogen atom or a carbon atom. It is particularly preferred that two or more fluorine-containing electron-withdrawing groups are directly bonded to .

Preferred fluorine-containing organic acids include, for example, compounds represented by the following formulas (411) to (416).
In the fluorine-containing organic acid represented by the following formula (411) (which may be abbreviated as “Nf ₂ NH” in this specification), a hydrogen atom donated as a proton is bonded to a nitrogen atom. , two fluoroalkylsulfonyl groups (more specifically, nonafluorobutanesulfonyl groups) are bonded to this nitrogen atom.
In the fluorine-containing organic acid represented by the following formula (412) (which may be abbreviated as “Tf ₂ NH” in this specification), a hydrogen atom donated as a proton is bonded to a nitrogen atom. , two fluoroalkylsulfonyl groups (more specifically, trifluoromethanesulfonyl groups) are bonded to this nitrogen atom.
In the fluorine-containing organic acid represented by the following formula (413) (in this specification, HN(SO ₂ CF ₂ ) ₂ CF ₂ ), a hydrogen atom donated as a proton is bonded to a nitrogen atom, Two fluoroalkylenesulfonyl groups (more specifically, difluoromethylenesulfonyl groups) are bonded to this nitrogen atom, and these groups are bonded to each other to form a ring.
In the fluorine-containing organic acid represented by the following formula (414) (which may be abbreviated as “Tf ₂ (C ₆ F ₅ )CH” in this specification), the hydrogen atom donated as a proton is carbon Two fluoroalkylsulfonyl groups (more specifically, trifluoromethanesulfonyl group) and one fluoroaryl group (pentafluorophenyl group) are bonded to this carbon atom.
In the fluorine-containing organic acid represented by the following formula (415) (which may be abbreviated as “NfOH” in this specification), hydrogen atoms donated as protons are bonded to oxygen atoms. One fluoroalkylsulfonyl group (more specifically, nonafluorobutanesulfonyl group) is bonded to the oxygen atom.
In the fluorine-containing organic acid represented by the following formula (416) (which may be abbreviated as “TfOH” in this specification), a hydrogen atom donated as a proton is bonded to an oxygen atom. One fluoroalkylsulfonyl group (more specifically, a trifluoromethanesulfonyl group) is bonded to the oxygen atom.

[Lewis acid]
The Lewis acid may be a known one.
Preferred Lewis acids include, for example, metal sulfonates, metal sulfonimides, and metal halides.

Examples of the metal sulfonate include a compound represented by the following general formula (421) (in this specification, sometimes abbreviated as "M(OTf) _n "), and a compound represented by the following general formula (422). compounds (which may be abbreviated as “M(ONf) _n ” in this specification), and the like.
As the metal sulfonimide, for example, a compound represented by the following general formula (423) (in this specification, may be abbreviated as "M(NTf ₂ ) _n "), a compound represented by the following general formula (424) (In this specification, it may be abbreviated as “M(NNf ₂ ) _n ”) and the like.

（式中、Ｍは金属原子であり；ｎは１以上の整数である。）

(In the formula, M is a metal atom; n is an integer of 1 or more.)

In general formulas (421), (422), (423) and (424), M is a metal atom.
Preferred metal atoms include indium (In), zinc (Zn), copper (Cu), silver (Ag), gold (Au), bismuth (Bi), zirconium (Zr), scandium (Sc), mercury (Hg), gallium (Ga), iron (Fe), hafnium (Hf), and the like.

In general formulas (421), (422), (423) and (424), n is an integer of 1 or more and is determined according to the type of M.

Preferred metal sulfonates include, for example, those in which M is indium (In), copper (Cu), silver (Ag), bismuth (Bi) or scandium (Sc), and particularly preferred metal sulfonates include In ( OTf) ₃ , In(ONf) ₃ , Cu(OTf) ₂ , AgOTf, Bi(OTf) ₃ , Sc(OTf) ₃ and the like.

Preferred metal sulfonimides include, for example, those in which M is indium (In), and particularly preferred metal sulfonimides include In(NTf ₂ ) ₃ , AgNTf ₂ , In(NNf ₂ ) ₃ and the like. .

Preferred metal halides include, for example, aluminum chloride (AlCl ₃ ), silver hexafluoroantimonate (V) (AgSbF ₆ ), and the like.

The acid catalyst to be coexisted during the reaction of compound (1) and compound (2) may be one kind or two or more kinds. The ratio can be appropriately adjusted depending on the purpose.
For example, the acid catalyst to be coexisted during the reaction may be only one or two or more Bronsted acids, or may be one or two or more Lewis acids. It may be both one or more Bronsted acids and one or more Lewis acids.

When using compound (1) in which R ¹ is a hydrogen atom, the amount of compound (3) produced can be increased by using only Bronsted acid as an acid catalyst or by using both Bronsted acid and Lewis acid. tend to increase.
When a metal halide is used as the acid catalyst, it is preferable to use a Lewis acid other than the metal halide.

The amount of the acid catalyst to be used may be appropriately adjusted according to the types of compound (1) and compound (2).
The amount of the acid catalyst used is preferably 1 to 50 mol%, more preferably 3 to 45 mol%, for example, either 3 to 35 mol% or 3 to 25 mol%. 7 to 45 mol%, 17 to 45 mol%, and 27 to 45 mol%, or 7 to 35 mol%, and 7 to 25 mol% good too. When the amount of the acid catalyst used is at least the lower limit, the reaction rate between compound (1) and compound (2) is further improved. Excessive use of the acid catalyst is suppressed because the amount of the acid catalyst used is equal to or less than the upper limit.

<Other ingredients>
In addition to the compound (1), the compound (2), and the acid catalyst, other components that do not fall under any of these may be used during the reaction within a range that does not impair the effects of the present invention.
The type of the other component can be arbitrarily selected according to the purpose, and is not particularly limited.

When the other component is used, the other component may be used alone or in combination of two or more. When two or more are used in combination, the combination and ratio thereof are It can be adjusted appropriately according to the purpose.

[solvent]
Preferred other components include, for example, solvents.
That is, the reaction may be carried out using a solvent or without using a solvent, but is preferably carried out using a solvent.
Examples of the solvent include ethers (compounds having an ether bond) such as 1,4-dioxane, tetrahydrofuran, tetrahydropyran, dibutyl ether and 1,2-dimethoxyethane; alcohols such as ethanol and isopropyl alcohol; ethyl acetate and acetic acid. Esters such as butyl; 1,2-dichloroethane, methylene chloride, halogenated hydrocarbons such as chlorobenzene (hydrocarbons having halogen atoms as substituents); nitriles such as propionitrile and acetonitrile (compounds having a cyano group); toluene , n-hexane, and hydrocarbons such as methylcyclohexane.

When a solvent is used, the solvent may be used alone or in combination of two or more. When two or more are used in combination, the combination and ratio thereof may be appropriately selected according to the purpose. Adjustable.

The amount of solvent used is not particularly limited, but for example, the concentration of compound (2) in the reaction solution is preferably 0.01 to 3 mol/L, more preferably 0.02 to 1.5 mol/L. so it can be adjusted.

<Other reaction conditions>
The reaction temperature may be appropriately adjusted and is not particularly limited.
The reaction temperature is preferably 40 to 120°C, for example, it may be either 45 to 120°C or 55 to 120°C, 45 to 115°C and 55 to 105°C.

The reaction time is not particularly limited and may be appropriately adjusted according to other conditions such as the reaction temperature so that the amount of compound (3) produced increases.
The reaction time is, for example, preferably 2 to 72 hours, more preferably 2 to 60 hours.

In this embodiment, after the completion of the reaction, the compound (3) can be taken out by a known method after post-treatment by a known method, if necessary.
For example, after completion of the reaction, post-treatment operations such as filtration, washing, extraction, pH adjustment, dehydration, concentration, etc. are carried out either singly or in combination of two or more as appropriate, and then concentration, crystallization, Compound (3) can be isolated by reprecipitation, column chromatography, or the like. Further, the extracted compound (3) may be subjected to any one of operations such as crystallization, reprecipitation, column chromatography, extraction, stirring and washing of the crystals with a solvent, or a combination of two or more of them, if necessary. Purification may be done by performing one or more times.
After the completion of the reaction, when another step using compound (3) is subsequently performed, after the completion of the reaction, post-treatment is performed by a known method as necessary, and then the above-described reaction is continued without taking out compound (3). Other steps may be performed.

The structure of compound (3) can be determined, for example, by nuclear magnetic resonance (NMR) spectroscopy, mass spectroscopy (MS), infrared spectroscopy (IR), ultraviolet/visible spectroscopy (UV-VIS absorption spectrum), elemental analysis. It can be confirmed by a known method such as.

The reaction of compound (1) and compound (2) in the coexistence of an acid catalyst is presumed to proceed through the route shown below.
That is, in the presence of an acid catalyst, two molecules of compound (1) undergo a nucleophilic addition reaction at the carbon atom at the 3-position with respect to the carbon atom constituting the carbonyl group in compound (2), Dehydration produces compound (3a) as an intermediate.
Next, after a proton (H ⁺ ) is bonded to the oxygen atom forming the ether bond in the compound (3a), a protonated product of the compound (3a) (wherein, the general formula (3a′) In this specification, sometimes referred to as “compound (3a′)”), the carbon atom corresponding to the 3-position of one compound (1)-derived site and the compound (2)-derived site Of the carbon atoms, a bond is newly formed between the carbon atom that is adjacent to the carbon atom to which the compound (1)-derived site is originally bonded and that is bonded to the oxygen atom; The bond between the carbon atom on which the bond is formed and the oxygen atom bonded to this carbon atom is broken to form a hydroxyl group. As a result, one compound (1)-derived site and compound (2)-derived site newly form a three-membered ring, the bicyclo structure disappears at the compound (2)-derived site, and an intermediate of the following general formula ( A compound represented by 3b) (which may be referred to herein as "compound (3b)") is produced. The order in which the formation of the new bond between the carbon atoms and the breakage of the bond between the carbon atom and the oxygen atom occur when the compound (3b) is produced is not particularly limited.
Next, in the compound (3b), the single bond between the carbon atom corresponding to the 3-position of the other compound (1)-derived site and the carbon atom of the compound (2)-derived site becomes a double bond. , the single bond between the previously formed carbon atoms between the one compound (1)-derived site and the compound (2)-derived site is cut, and as a result, this one compound (1) The site of origin metastasizes. As a result, a compound represented by the following general formula (3c) (in this specification, may be referred to as "compound (3c)") is produced as an intermediate.
Next, among the carbon atoms in the compound (2)-derived site, a hydrogen atom is eliminated from the carbon atom to which one of the compound (1)-derived sites after the transfer is bonded, and along with this, the compound (2)-derived site The double bond between the carbon atom of and the site derived from the other compound (1) becomes a single bond, resulting in a protonated compound represented by the following general formula (3d) (in this specification may be referred to as "compound (3d)").
Next, in the coexistence of an acid catalyst, dehydration occurs at the compound (2)-derived site in the compound (3d) to form an aromatic ring, thereby producing the desired compound (3).
In each of the above intermediates, that is, compound (3a), compound (3a′), compound (3b), compound (3c) and compound (3d), R ⁷ , R ⁸ and R ⁹ are bonded A six-membered ring has no aromatic character. Therefore, it is speculated that the electronic properties of R ⁷ , R ⁸ and R ⁹ do not significantly affect the reaction of these intermediates. In particular, R ⁷ and R ⁸ are not involved in electron transfer or hydrogen atom elimination in each reaction from compound (3a) to compound (3d), and are not involved in the substitution position on the six-membered ring Also from the viewpoint of , its electronic and steric properties are presumed not to significantly affect the reaction of the intermediate.

（式中、Ｒ^１、Ｒ^２、Ｒ^３、Ｒ^４、Ｒ^５、Ｒ^６、Ｒ^７、Ｒ^８及びＲ^９は、上記と同じである。）

(Wherein, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ and R ⁹ are the same as above.)

In the above route, compound (3b), compound (3c) and compound (3d) are all difficult to isolate, and their structures are also difficult to determine, so the production of these intermediates is speculative.
In contrast, compound (3a) is relatively stable and can be removed. Compound (3a) is a novel compound.
The formation of compound (3) from compound (3a) is rationalized by assuming three intermediates, compound (3b), compound (3c) and compound (3d).
In the route described above, it is presumed that, after the production of compound (3a), if other raw material compounds coexist, a compound having a structure different from that of compound (3) will be the final product. On the other hand, in the present embodiment, by allowing the reaction to proceed as it is without coexisting such other raw material compounds, various compounds can be easily and efficiently obtained as the target compound (3). can get. In the present embodiment, such excellent effects can be obtained by selecting compound (2) as a raw material for producing diindolylbenzenes.

Compound (3a) can be efficiently produced by, for example, reacting in the same manner as in the above-described production method of compound (3) and stopping the reaction in the middle. At this time, the reaction conditions may be changed so as to reduce the amount of compound (3) produced.
That is, as a method for producing compound (3a), for example, compound (1) and compound (2) are reacted in the presence of an acid catalyst to obtain compound (3a).

The structure of compound (3a) can be determined, for example, by nuclear magnetic resonance (NMR) spectroscopy, mass spectroscopy (MS), infrared spectroscopy (IR), ultraviolet/visible spectroscopy, as in the case of compound (3). It can be confirmed by known techniques such as method (UV-VIS absorption spectrum) and elemental analysis.

Compound (3a) can be isolated, for example, in the same manner as compound (3). That is, after completion of the reaction, post-treatment operations such as filtration, washing, extraction, pH adjustment, dehydration, concentration, etc. are carried out either singly or in combination of two or more as appropriate, and then concentration, crystallization, Compound (3a) can be isolated by reprecipitation, column chromatography, or the like. Further, the extracted compound (3a) may be subjected to any one of operations such as crystallization, reprecipitation, column chromatography, extraction, stirring and washing of the crystals with a solvent, or a combination of two or more of them, if necessary. Purification may be done by performing one or more times.
After the compound (3a) is produced by the reaction, after the completion of the reaction, the next step may be performed without taking out the compound (3a) after post-treatment by a known method as necessary. . By omitting the removal of compound (3a) in this way, compound (3) can be produced more efficiently.

The present invention will be described in more detail below with reference to specific examples. However, the present invention is by no means limited to the examples shown below.

All amounts (mol %) of the acid catalyst used below are based on the compound (2).
The yield of compound (3) is based on compound (2) regardless of whether it is the isolated yield or the NMR conversion yield described later. The NMR-converted yield (%) is the yield obtained from NMR measurement data when nitromethane is used as an internal standard.
“mmol” indicates “10 ⁻³ mol” and “μmol” indicates “10 ⁻⁶ mol”.

In the following, the names of individual compounds such as compound (1), compound (2), compound (3), and compound (3a) are determined using the symbols attached to the formulas representing these compounds. For example, a compound represented by formula (1101) described later is referred to as compound (1101).

<<Production of Compound (3)>>
[Example 1]
Under the conditions shown in Table 1, as shown in the following formula, compound (1), compound (1101), and compound (2), compound (2101), are reacted to obtain compound (3) as compound (3101). ). More specifically, it is as follows.
That is, under reduced pressure, the container was heat-treated at 450° C. for 3 minutes using a heat gun, then cooled to room temperature, and the atmosphere was replaced with argon gas. Then, 1,4-dioxane (1.5 mL), TfOH (15 mol%) and compound (2101) (7-oxabicyclo[2.2.1]-5-hepten-2-one) ( 0.3 mmol) and compound (1101) (1-methylindole) (0.75 mmol) were added and reacted at 60° C. for 16 hours.
After completion of the reaction, saturated sodium bicarbonate aqueous solution (0.5 mL) was added to the reaction solution, the aqueous layer was extracted three times with ethyl acetate (5 mL), and the resulting organic layer was washed with saturated brine (1 mL), After dehydration with anhydrous sodium sulfate, filtration with a cotton plug, and concentration under reduced pressure. Using a mixed solvent of n-hexane and ethyl acetate as a mobile phase, the concentrate obtained above was purified by silica gel column chromatography to obtain the target compound (3101) (yield: 86.0 mg ). The isolated yield of the compound (3101) was 83%, and the NMR converted yield was 84%, and the NMR converted yield almost matched the isolated yield. The yields listed in Table 1 are isolated yields. Unless otherwise specified, this also applies to other examples below.
The NMR data of the obtained compound (3101) are shown below.

¹ H NMR (500 MHz, CDCl ₃ ) δ3.61 (s, 6 H), δ6.69 (s, 2 H), δ7.02 (t, J = 7.4 Hz, 2 H), δ7.18 (t , J = 7.7 Hz, 2 H), δ7.26 (d, J = 8.0 Hz, 2 H), δ7.35-7.38 (m, 2 H), δ7.54 (d, J = 8.0 Hz, 2 H ), δ7.63-7.65 (m, 2 H).
^13C {1H} NMR (125 MHz, _CDCl3 ) δ32.6, 109.0, 115.8, 119.2, 120.1, 121.3, 126.3, 127.4, 128.1, 131.2, 134.0, 136.6.

[Example 2]
Compound (3102), the target compound, was prepared in the same manner as in Example 1, except that compound (1102) and compound (2101) were reacted under the conditions shown in Table 1 as shown in the following formula. (yield 52.5 mg, isolated yield 45%).
The NMR data of the obtained compound (3102) are shown below.

¹ H NMR (500 MHz, CDCl ₃ ) δ6.80 (d, J = 2.3 Hz, 2 H), δ7.01 (t, J = 7.7 Hz, 2 H), δ7.15 (t, J = 7.4 Hz , 2 H), δ7.30 (d, J = 8.0 Hz, 2 H), δ7.39-7.43 (m, 2 H), δ7.53 (d, J = 8.0 Hz, 2 H), δ7.66 -7.69 (m, 2H), δ7.88 (br, 2H).
¹³ C{1H} NMR (125 MHz, _CDCl3 ) δ111.1, 117.4, 119.9, 120.1, 121.9, 123.5, 126.7, 127.0, 131.3, 134.3, 135.8.

[Example 3]
The target compound (3103) was obtained in the same manner as in Example 1, except that the compound (1103) and the compound (2101) were reacted under the conditions shown in Table 1 as shown in the following formula. (yield 76.6 mg, isolated yield 65%).
The NMR data of the obtained compound (3103) are shown below.

¹ H NMR (500 MHz, CDCl ₃ ) δ1.23 (d, J = 6.9, 12 H), δ4.47-4.55 (m, 2 H), δ7.01 (t, J = 7.7 Hz, 2 H) , δ7.15 (t, J = 7.4 Hz, 2 H), δ7.30 (d, J = 8.0 Hz, 2 H), δ7.36-7.39 (m, 2 H), δ7.53 (d, J = 8.0 Hz, 2 H), δ7.66-7.70 (m, 2 H), δ7.88 (s, 2 H).
¹³ C{1H} NMR (125 MHz, _CDCl3 ) δ111.1, 117.4, 119.9, 120.1, 121.9, 123.5, 126.7, 127.0, 131.3, 134.3, 135.8.

[Example 4]
Compound (3104), the target product, was prepared in the same manner as in Example 1, except that compound (1104) and compound (2101) were reacted under the conditions shown in Table 1 as shown in the following formula. (yield 76.6 mg, isolated yield 84%).
The NMR data of the obtained compound (3104) are shown below.

¹ H NMR (500 MHz, CDCl ₃ ) δ0.81 (t, J = 7.3, 6 H), δ1.06 (td, J = 15.0, 7.6 Hz, 4 H), δ1.49-1.57 (m, 4 H), δ3.92 (t, J = 7.1 Hz, 4 H), δ6.73 (s, 2 H), δ6.96 (t, J = 7.6 Hz, 2 H), δ7.13 (t, J = 7.6 Hz, 2 H), δ7.25 (d, J = 8.7 Hz, 2 H), δ7.35-7.39 (m, 2 H), δ7.50 (d, J = 8.2 Hz, 2 H), δ7.63-7.68 (m, 2H).
¹³ C{1H} NMR (125 MHz, _CDCl3 ) δ13.9, 15.4, 20.0, 32.3, 45.9, 66.0, 109.3, 115.9, 119.3, 120.3, 121.2, 126.4, 123.7, 131.2, 134.3, 136.0.

[Example 5]
The target compound (3105) was obtained in the same manner as in Example 1, except that the compound (1105) and the compound (2101) were reacted under the conditions shown in Table 1 as shown in the following formula. (Yield 136.4 mg, isolated yield 91%).
The NMR data of the obtained compound (3105) are shown below.

¹ H NMR (400 MHz, CDCl ₃ ) δ5.13 (s, 4 H), δ6.76 (d, J = 6.4 Hz, 4 H), δ6.86 (s, 2 H), δ6.95-6.99 (m, 2 H), δ7.09-7.17 (m, 10 H), δ7.37-7.41 (m, 2 H), δ7.50 (d, J = 8.2 Hz, 2 H), δ7.64- 7.68 (m, 2H).
^13C NMR {1H} (125 MHz, _CDCl3 ) δ50.0, 109.7, 117.0, 119.7, 120.4, 121.7, 126.4, 126.6, 127.4, 127.5, 127.6, 128.8, 131.3, 134.2, 1 36.2, 137.5.

[Example 6]
The target compound (3106) was obtained in the same manner as in Example 1, except that the compound (1106) and the compound (2101) were reacted under the conditions shown in Table 1 as shown in the following formula. (Yield 103.7 mg, isolated yield 74%).
The NMR data of the obtained compound (3106) are shown below.

¹ H NMR (500 MHz, CDCl ₃ ) δ7.05-7.08 (m, 4 H), δ7.18-7.21 (m, 6 H), δ7.30 (t, J = 7.4 Hz, 2 H), δ7 .43 (t, J = 7.7 Hz, 4 H), δ7.47-7.51 (m, 2 H), δ7.54 (d, J = 8.0 Hz, 2 H), δ7.58 (d, J = 7.4 Hz, 2 H), δ7.80-7.83 (m, 2 H).
¹³ C{1H} NMR (125 MHz, _CDCl3 ) δ110.4, 118.2, 120.6, 122.4, 124.4, 126.5, 127.0, 127.5, 128.1, 129.6, 131.1, 133.8, 136.0, 139.6.

［実施例７］
表１に示す条件で、下記式に示すように、化合物（１１０７）と化合物（２１０１）とを反応させた点以外は、実施例１の場合と同様にして、目的物である化合物（３１０７）を得た（収量１０５．６ｍｇ、単離収率６７％）。
得られた化合物（３１０７）のＮＭＲデータを以下に示す。

[Example 7]
Compound (3107), the target compound, was prepared in the same manner as in Example 1, except that compound (1107) and compound (2101) were reacted under the conditions shown in Table 1 as shown in the following formula. (Yield 105.6 mg, isolated yield 67%).
The NMR data of the obtained compound (3107) are shown below.

¹ H NMR (400 MHz, CDCl ₃ ) δ3.83 (s, 6 H), δ6.91-7.06 (m, 12 H), δ7.15 (t, J = 7.6 Hz, 2 H), δ7.39 (d, J = 8.2 Hz, 2 H), δ7.42-7.47 (m, 2 H), δ7.53 (d, J = 7.8 Hz, 2 H), δ7.75-7.79 (m, 2 H) .
¹³ C{1H} NMR (125 MHz, _CDCl3 ) δ55.7, 110.3, 114.7, 117.6, 120.3, 120.5, 122.2, 126.0, 126.9, 127.7, 127.9, 131.1, 132.6, 133.9, 1 58.2.

[Example 8]
Compound (3108), the target compound, was prepared in the same manner as in Example 1, except that compound (1108) and compound (2101) were reacted under the conditions shown in Table 1 as shown in the following formula. (Yield 105.2 mg, isolated yield 47%).
The NMR data of the obtained compound (3108) are shown below.

¹ H NMR (500 MHz, CDCl ₃ ) δ7.17 (t, J = 7.6 Hz, 2 H), δ7.34-7.47 (m, 4 H), δ7.73-7.77 (m, 2 H).
¹³ C{1H} NMR (125 MHz, _CDCl3 ) δ110.2, 118.8, 119.8, 120.8, 120.9, 122.8, 125.8, 125.9, 127.2, 128.2, 131.3, 132.8, 132.9, 133.6, 135.8, 138.6.

[Example 9]
The target compound (3401) was obtained in the same manner as in Example 1, except that the compound (1401) and the compound (2101) were reacted under the conditions shown in Table 1 as shown in the following formula. (yield 46.7 mg, isolated yield 39%).
The NMR data of the obtained compound (3401) are shown below.

¹ H NMR (500 MHz, CDCl ₃ ) δ3.43 (s, 6 H), δ3.59 (s, 6 H), δ6.76-6.80 (m, 6 H), δ7.11 (d, J = 8.6 Hz, 2 H), δ7.37-7.40 (m, 2 H), δ7.61-7.64 (m, 2 H).
^13C {1H} NMR (125 MHz, _CDCl3 ) δ33.0, 55.5, 101.4, 109.9, 112.1, 116.0, 126.5, 127.3, 128.8, 131.3, 132.1, 134.3, 154.0.

[Example 10]
The target compound (3402) was obtained in the same manner as in Example 1, except that the compound (1402) and the compound (2101) were reacted under the conditions shown in Table 1 as shown in the following formula. got In this example, it was confirmed by NMR that compound (3402) was obtained without isolation of compound (3402) by silica gel column chromatography. The NMR conversion yield of compound (3402) obtained from NMR data was 30% (*).
The NMR data of the obtained compound (3402) are shown below.

¹ H NMR (500 MHz, CDCl ₃ ) δ3.85 (s. 6 H), δ6.94 (d, J = 2.29, 2 H), δ8.20 (br, 2 H).

[Example 11]
The target compound (3403) was obtained in the same manner as in Example 1, except that the compound (1403) and the compound (2101) were reacted under the conditions shown in Table 1 as shown in the following formula. (Yield 132.3 mg, isolated yield 88%).
The NMR data of the obtained compound (3403) are shown below.

¹ H NMR (500 MHz, CDCl ₃ ) δ3.62 (s, 6 H), δ6.75 (s, 2 H), δ7.07 (d, J = 8.6 Hz, 2 H), δ7.17 (d , J = 8.6 Hz, 2 H), δ7.38-7.40 (m, 2 H), δ7.44 (s, 2 H), δ7.54-7.57 (m, 2 H).
^13C {1H} NMR (125 MHz, _CDCl3 ) δ32.9, 110.6, 112.7, 115.9, 122.6, 124.2, 126.9, 128.9, 129.0, 131.2, 133.6, 135.3.

[Example 12]
Compound (3201), the target compound, was prepared in the same manner as in Example 1, except that compound (1201) and compound (2101) were reacted under the conditions shown in Table 1 as shown in the following formula. got In this example, it was confirmed by NMR that compound (3201) was obtained without isolation of compound (3201) by silica gel column chromatography. Compound (3201) was confirmed to be a mixture of two stereoisomers, ie, an anti compound (3201-1) and a syn compound (3201-2). The NMR conversion yield of compound (3201-1) obtained from NMR data was 18% (*), and the NMR conversion yield of compound (3201-2) was 32% (*), for a total of 50%. Met.
The NMR data of the obtained compound (3201-1) and compound (3201-2) are shown below.

Compound (3201a-1):
¹ H NMR (500 MHz, CDCl ₃ ) δ1.55 (s, 6 H), δ7.69 (br, 2 H).
Compound (3201b-2):
¹ H NMR (500 MHz, CDCl ₃ ) δ2.41 (s, 6 H), δ7.59-7.63 (m, 2 H), δ7.76 (br, 2 H).

[Example 13]
Compound (3202), the target compound, was prepared in the same manner as in Example 1, except that compound (1202) and compound (2101) were reacted under the conditions shown in Table 1 as shown in the following formula. got Compound (3202) was confirmed to be a mixture of two stereoisomers, namely, anti-isomer compound (3202-1) and syn-isomer compound (3202-2). The molar ratio of these compounds was Compound (3202-1):Compound (3202-2)=29:71. The total isolated yield of compound (3202-1) and compound (3202-2) was 41.1 mg, and the total isolated yield was 36%.
The NMR data of the obtained compound (3202-1) and compound (3202-2) are shown below.

Compound (3201-1):
¹ H NMR (500 MHz, CDCl ₃ ) δ1.54 (s, 6 H), δ3.47 (s, 6 H), δ7.06-7.10 (m, 2 H), δ7.13-7.17 (m, 2H).
Compound (3201-2):
¹ H NMR (500 MHz, CDCl ₃ ) δ2.06 (s, 6 H), δ3.48 (s, 6 H), δ6.74 (t, J = 7.4 Hz, 2 H), δ6.99 (t , J = 8.0 Hz, 2 H), δ7.49-7.53 (m, 2 H).

[Example 14]
The target compound (3203) was obtained in the same manner as in Example 1, except that the compound (1203) and the compound (2101) were reacted under the conditions shown in Table 1 as shown in the following formula. got Compound (3203) was confirmed to be a mixture of two stereoisomers, ie, an anti compound (3203-1) and a syn compound (3203-2). The molar ratio of these compounds was compound (3203-1): compound (3203-2)=31:69. The total isolated yield of compound (3203-1) and compound (3203-2) was 47.9 mg, and the total isolated yield was 32%.
The NMR data of the obtained compound (3203-1) and compound (3203-2) are shown below.

Compound (3203-1):
¹ H NMR (500 MHz, CDCl ₃ ) δ1.54 (s, 6 H), δ3.47 (s, 6 H), δ7.06-7.10 (m, 2 H), δ7.13-7.17 (m, 2H).
^13C {1H} NMR (125 MHz, _CDCl3 ) δ30.9.
Compound (3203-2):
¹ H NMR (500 MHz, CDCl ₃ ) δ2.06 (s, 6 H), δ3.48 (s, 6 H), δ6.74 (t, J = 7.4 Hz, 2 H), δ6.99 (t , J = 8.0 Hz, 2 H), δ7.49-7.53 (m, 2 H).
^13C {1H} NMR (125 MHz, _CDCl3 ) δ31.0.

[Example 15]
The target compound (3204) was obtained in the same manner as in Example 1 except that the compound (1204) and the compound (2101) were reacted under the conditions shown in Table 1 as shown in the following formula. got Compound (3204) was confirmed to be a mixture of two stereoisomers, ie, an anti compound (3204-1) and a syn compound (3204-2). The molar ratio of these compounds was Compound (3204-1):Compound (3204-2)=22:78. The total isolated yield of compound (3204-1) and compound (3204-2) was 30.1 mg, and the total isolated yield was 16%.
The NMR data of the obtained compound (3204-1) and compound (3204-2) are shown below.

Compound (3204-1):
¹ H NMR (500 MHz, CDCl ₃ ) δ6.32 (d, J = 7.5 Hz, 2 H), δ7.13 (d, J = 6.9 Hz, 2 H), δ7.36-7.39 (m, 2 H ).
Compound (3204-2):
¹ H NMR (500 MHz, CDCl ₃ ) δ6.37-6.40 (m, 2 H), δ7.47-7.51 (m, 2 H), δ7.69-7.72 (m, 2 H).

<<Production of compound (3a) and compound (3)>>
[Example 16]
<Production of compound (3a)>
During the production of compound (3101) in Example 1, the production of compound (3101a), which is a reaction intermediate thereof, was confirmed. The reaction was carried out under the same conditions as for . Then, the compound (3101a) was separately isolated by silica gel column chromatography.
The NMR data of the obtained compound (3101a) are shown below.

¹ H NMR (500 MHz, CDCl ₃ ) δ2.32 (d, J = 11.4 Hz, 1 H), δ2.58 (dd, J = 11.2 Hz, 4.8, 1 H), δ3.72 (s, 3 H ), δ3.73 (s, 3 H), δ5.21 (d, J = 4.6 Hz, 1 H), δ5.78 (s, 1 H), δ5.99 (d, J = 5.5 Hz, 1 H ), δ6.38 (d, J = 5.5 Hz, 1 H), δ6.83-6.91 (m, 3 H), δ5.99 (d, J = 5.5 Hz, 1 H), δ7.05-7.11 ( m, 3 H), δ7.18 (dd, J = 8.0, 3.0 Hz, 2 H), δ7.44 (t, J = 8.7 Hz, 2 H).
^13C {1H} NMR (125 MHz, _CDCl3 ) δ32.7, 32.8, 40.6, 44.3, 79.3, 85.0, 108.9, 109.0, 118.2, 118.5, 119.8, 120.8, 120.9, 121.0, 121.3, 122.3, 125.4, 126.6 , 127.2.

The compound ( _3101a )was gotten.

<Production of compound (3)>
Then, in the same manner as in Example 1, 1,4-dioxane (0.5 mL), compound (3101a) (0.3 mmol), and TfOH (compound (15 mol % based on (3101a)) and water (0.3 mmol) were added and reacted at 60° C. for 8 hours to obtain the target compound (3101). In this example, it was confirmed by NMR that compound (3101) was obtained without isolation of compound (3101) by silica gel column chromatography. The NMR conversion yield of compound (3101) obtained from NMR data was 68% (*).
It was confirmed that the NMR data of the obtained compound (3101) was the same as in Example 1.

<<Production of compound (3a) and compound (3)>>
[Examples 17 to 27]
As shown in Table 2, the target compound (3101) was obtained in the same manner as in Example 1, except that TfOH was replaced with another acid catalyst. In Example 21, the acid catalyst HBF ₄ was used as an aqueous solution with a concentration of 42% by weight.
The NMR data of the obtained compound (3101) were the same as in Example 1 in all cases.
The NMR conversion yield (*) of the obtained compound (3101) is shown in Table 2 together with the NMR conversion yield (*) of the compound (3101a) produced at the same time. Table 2 also shows the conditions and results of Example 1.

[Comparative Example 1]
As shown in Table 2, an attempt was made to produce the target compound (3101) in the same manner as in Example 1, except that TfOH (15 mol %) was not used.
However, by NMR, almost no compound (3101) or compound (3101a) was produced, and almost no starting compound (2101) remained, indicating that a large amount of by-products were produced. confirmed.

<<Production of compound (3a) and compound (3)>>
[Examples 28-36]
As shown in Table 3, in the same manner as in Example 1, except that another solvent (1.5 mL) was used instead of 1,4-dioxane (1.5 mL). Compound (3101) was obtained.
Among various solvents, dibutyl ether (Example 29), 1,2-dimethoxyethane (Example 30), ethanol (Example 31), ethyl acetate (Example 32), and 1,2-dichloroethane (Example In Example 33), the product that had been stored in the presence of molecular sieve 4A was used.
The NMR data of the obtained compound (3101) were the same as in Example 1 in all cases.
The NMR conversion yield (*) of the obtained compound (3101) is shown in Table 3 together with the NMR conversion yield (*) of the compound (3101a) produced at the same time. Table 3 also shows the conditions and results of Example 1.

<<Production of compound (3)>>
[Examples 37-41]
The target compound (3101) was obtained in the same manner as in Example 1, except that the reaction conditions were changed as shown in Table 4.
In these examples, mainly the reaction temperature or reaction time was changed from each other.
The NMR data of the obtained compound (3101) were the same as in Example 1 in all cases.
Table 4 shows the NMR conversion yield (*) of the obtained compound (3101). In addition, the examples in which compound (3101) was isolated by silica gel column chromatography are shown in Table 4 together with the isolation yield as numerical values in parentheses. For example, in Example 39, the NMR converted yield (*) is 30% and the isolated yield is 33%. This also applies to the following examples and comparative examples.

[Examples 42 to 47]
The target compound (3101) was obtained in the same manner as in Example 1, except that the reaction conditions were changed as shown in Table 5.
In these examples, the type of acid catalyst was changed.
The NMR data of the obtained compound (3101) were the same as in Example 1 in all cases.
Table 5 shows the NMR conversion yield (*) of the obtained compound (3101). In addition, the examples in which the compound (3101) was isolated by silica gel column chromatography are shown in Table 5 together with the isolation yield as numerical values in parentheses. Table 5 also shows the conditions and results of Example 39.

[Comparative Example 2]
As shown in Table 5, production of the target compound (3101) was attempted in the same manner as in Example 39, except that In(NTf ₂ ) ₃ (10 mol %) was not used.
However, according to NMR, almost no compound (3101) or compound (3101a) was produced, more than half of the starting compound (2101) disappeared, and a large amount of by-products were produced. was confirmed to occur.

[Examples 48-54]
The target compound (3101) was obtained in the same manner as in Example 1, except that the reaction conditions were changed as shown in Table 6.
In these Examples, the type of reaction solvent was changed mutually.
The NMR data of the obtained compound (3101) were the same as in Example 1 in all cases.
Table 6 shows the NMR conversion yield (*) of the obtained compound (3101). In addition, the examples in which the compound (3101) was isolated by silica gel column chromatography are shown in Table 6 together with the isolation yield as numerical values in parentheses. Table 6 also shows the conditions and results of Example 39.

[Examples 55-58]
The target compound (3101) was obtained in the same manner as in Example 1, except that the reaction conditions were changed as shown in Table 7.
In these examples, the amount of compound (1) used was changed.
The NMR data of the obtained compound (3101) were the same as in Example 1 in all cases.
Table 7 shows the NMR conversion yield (*) of the obtained compound (3101). As for the examples in which the compound (3101) was isolated by silica gel column chromatography, the isolation yield is also shown in Table 7 as parenthesized figures. Table 7 also shows the conditions and results of Example 39.

[Examples 59-70]
The target compound (3101) was obtained in the same manner as in Example 1, except that the reaction conditions were changed as shown in Table 8.
In these examples, mainly the amount of acid catalyst used, the amount of reaction solvent used, or the reaction time was changed.
The NMR data of the obtained compound (3101) were the same as in Example 1 in all cases.
Table 8 shows the NMR conversion yield (*) of the obtained compound (3101). In addition, the examples in which the compound (3101) was isolated by silica gel column chromatography are shown in Table 8 together with the isolation yield as numerical values in parentheses. Table 8 also shows the conditions and results of Example 57.

[Examples 71 to 76]
The target compound (3101) was obtained in the same manner as in Example 1, except that the reaction conditions were changed as shown in Table 9.
In these examples, the type of acid catalyst was changed.
In addition, in Examples 72 and 74, the reaction was carried out under light-shielding conditions (**).
The NMR data of the obtained compound (3101) were the same as in Example 1 in all cases.
Table 9 shows the NMR conversion yield (*) of the obtained compound (3101). In addition, the examples in which the compound (3101) was isolated by silica gel column chromatography are shown in Table 9 together with the isolation yield as numerical values in parentheses. Table 9 also shows the conditions and results of Example 39.

[Examples 77 to 81]
The target compound (3101) was obtained in the same manner as in Example 1, except that the reaction conditions were changed as shown in Table 10.
In these examples, the acid catalyst was fixed to AgOTf, and the amount used, reaction temperature or reaction time was varied.
The NMR data of the obtained compound (3101) were the same as in Example 1 in all cases.
Table 10 shows the NMR conversion yield (*) of the obtained compound (3101). In addition, the examples in which compound (3101) was isolated by silica gel column chromatography are shown in Table 10 together with the isolation yield as numerical values in parentheses.

[Examples 82-88]
The target compound (3101) was obtained in the same manner as in Example 1, except that the reaction conditions were changed as shown in Table 11.
In these examples, mainly the type of acid catalyst, the reaction temperature or the reaction time were changed from each other.
The NMR data of the obtained compound (3101) were the same as in Example 1 in all cases.
The NMR conversion yield (*) of the obtained compound (3101) is shown in Table 11 together with the NMR conversion yield (*) of the compound (3101a) produced at the same time. In addition, the examples in which compound (3101) was isolated by silica gel column chromatography are shown in Table 11 together with the isolation yield as numerical values in parentheses. Table 11 also shows the conditions and results of Example 1.

[Examples 89-93]
The target compound (3101) was obtained in the same manner as in Example 1, except that the reaction conditions were changed as shown in Table 12.
In these Examples, the type of Bronsted acid, the amount used, the reaction temperature or the reaction time were changed.
The NMR data of the obtained compound (3101) were the same as in Example 1 in all cases.
The NMR conversion yield (*) of the obtained compound (3101) is shown in Table 12 together with the NMR conversion yield (*) of the compound (3101a) produced at the same time. In addition, the examples in which compound (3101) was isolated by silica gel column chromatography are shown in Table 12 together with the isolation yield as numerical values in parentheses. Table 12 also shows the conditions and results of Examples 1 and 86.

INDUSTRIAL APPLICABILITY The present invention can be used as highly functional materials such as physiologically active substances and electronic materials, and for their production.

Claims (5)

A compound represented by the following general formula (3).

(wherein R ¹ and R ² are each independently a hydrogen atom, an aliphatic group, an aryl group, a heteroaryl group, an arylalkyl group, an alkylaryl group or a trialkylsilyl group; one or more hydrogen atoms in the group, heteroaryl group, arylalkyl group, alkylaryl group or trialkylsilyl group may be replaced by an alkoxy group, an aryloxy group or a halogen atom;
R ³ , R ⁴ , R ⁵ and R ⁶ are each independently a hydrogen atom, an aliphatic group, an aryl group, a heteroaryl group, an arylalkyl group, an alkylaryl group, a trialkylsilyl group, an alkoxy group, an alkenyloxy group , an aryloxy group, an arylalkyloxy group, an alkylaryloxy group, a hydroxyl group or a halogen atom, and one of the aliphatic groups, aryl groups, heteroaryl groups, arylalkyl groups, alkylaryl groups or trialkylsilyl groups or two or more hydrogen atoms may be substituted with an alkoxy group, an aryloxy group or a halogen atom;
R ⁷ , R ⁸ and R ⁹ are hydrogen atoms;
two R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁶ may be the same or different;
adjacent two of R ³ , R ⁴ , R ⁵ and R ⁶ bonded to the same ring skeleton are the aliphatic group, aryl group, heteroaryl group, arylalkyl group, alkylaryl group; When it is an organic group selected from a trialkylsilyl group, an alkoxy group, an alkenyloxy group, an aryloxy group, an arylalkyloxy group and an alkylaryloxy group, these two organic groups are bonded together to form a ring. may be formed. ) R ¹ is a hydrogen atom, an alkyl group, an aryl group, an arylalkyl group or an alkylaryl group, and one or more hydrogen atoms in the alkyl group, aryl group, arylalkyl group or alkylaryl group are , optionally substituted with a halogen atom or an alkoxy group,
R ² is a hydrogen atom, an alkyl group, an aryl group or an alkylaryl group, and one or more hydrogen atoms in the alkyl group, aryl group or alkylaryl group are substituted with a halogen atom or an alkoxy group may have been
2. The compound of claim 1, wherein said ^R3 , ^R4 , ^R5 and ^R6 are each independently a hydrogen atom, an alkyl group, an alkoxy group or a halogen atom. R ¹ is a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, a phenyl group or a benzyl group, and 1 to 3 hydrogen atoms in the phenyl group are an alkyl group having 1 to 3 carbon atoms or an alkoxy group; or optionally substituted with a halogen atom,
R ² is a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, or a phenyl group, and 1 to 3 hydrogen atoms in the phenyl group are an alkyl group having 1 to 3 carbon atoms, an alkoxy group, or a halogen atom may be replaced with
3. The compound according to claim 1 or 2, wherein said R ³ , R ⁴ , R ⁵ and R ⁶ are each independently a hydrogen atom, an alkyl or alkoxy group having 1 to 3 carbon atoms, or a halogen atom. A compound represented by the following general formula (3a).

(wherein R ¹ and R ² are each independently a hydrogen atom, an aliphatic group, an aryl group, a heteroaryl group, an arylalkyl group, an alkylaryl group or a trialkylsilyl group; one or more hydrogen atoms in the group, heteroaryl group, arylalkyl group, alkylaryl group or trialkylsilyl group may be replaced by an alkoxy group, an aryloxy group or a halogen atom;
R ³ , R ⁴ , R ⁵ and R ⁶ are each independently a hydrogen atom, an aliphatic group, an aryl group, a heteroaryl group, an arylalkyl group, an alkylaryl group, a trialkylsilyl group, an alkoxy group, an alkenyloxy group , an aryloxy group, an arylalkyloxy group, an alkylaryloxy group, a hydroxyl group or a halogen atom, and one of the aliphatic groups, aryl groups, heteroaryl groups, arylalkyl groups, alkylaryl groups or trialkylsilyl groups or two or more hydrogen atoms may be substituted with an alkoxy group, an aryloxy group or a halogen atom;
R ⁷ , R ⁸ and R ⁹ are hydrogen atoms;
two R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁶ may be the same or different;
adjacent two of R ³ , R ⁴ , R ⁵ and R ⁶ bonded to the same ring skeleton are the aliphatic group, aryl group, heteroaryl group, arylalkyl group, alkylaryl group; When it is an organic group selected from a trialkylsilyl group, an alkoxy group, an alkenyloxy group, an aryloxy group, an arylalkyloxy group and an alkylaryloxy group, these two organic groups are bonded together to form a ring. may be formed. ) A compound represented by the following general formula (1) and a compound represented by the following general formula (2) are reacted in the presence of an acid catalyst to obtain a compound represented by the following general formula (3). A method for producing a compound.

(wherein R ¹ and R ² are each independently a hydrogen atom, an aliphatic group, an aryl group, a heteroaryl group, an arylalkyl group, an alkylaryl group or a trialkylsilyl group; one or more hydrogen atoms in the group, heteroaryl group, arylalkyl group, alkylaryl group or trialkylsilyl group may be replaced by an alkoxy group, an aryloxy group or a halogen atom;
R ³ , R ⁴ , R ⁵ and R ⁶ are each independently a hydrogen atom, an aliphatic group, an aryl group, a heteroaryl group, an arylalkyl group, an alkylaryl group, a trialkylsilyl group, an alkoxy group, an alkenyloxy group , an aryloxy group, an arylalkyloxy group, an alkylaryloxy group, a hydroxyl group or a halogen atom, and one of the aliphatic groups, aryl groups, heteroaryl groups, arylalkyl groups, alkylaryl groups or trialkylsilyl groups or two or more hydrogen atoms may be substituted with an alkoxy group, an aryloxy group or a halogen atom;
R ⁷ , R ⁸ and R ⁹ are hydrogen atoms;
two R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁶ may be the same or different;
adjacent two of R ³ , R ⁴ , R ⁵ and R ⁶ bonded to the same ring skeleton are the aliphatic group, aryl group, heteroaryl group, arylalkyl group, alkylaryl group; When it is an organic group selected from a trialkylsilyl group, an alkoxy group, an alkenyloxy group, an aryloxy group, an arylalkyloxy group and an alkylaryloxy group, these two organic groups are bonded together to form a ring. may be formed. )