JPH06211780A - Benzoyl cyanide derivative, its production and reaction using the same - Google Patents
Benzoyl cyanide derivative, its production and reaction using the sameInfo
- Publication number
- JPH06211780A JPH06211780A JP2363693A JP2363693A JPH06211780A JP H06211780 A JPH06211780 A JP H06211780A JP 2363693 A JP2363693 A JP 2363693A JP 2363693 A JP2363693 A JP 2363693A JP H06211780 A JPH06211780 A JP H06211780A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound
- reaction
- compound represented
- cyanide
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は農医薬中間体として有用
な新規なベンゾイルシアナイド誘導体、その製法及びそ
れを用いた反応に関する。FIELD OF THE INVENTION The present invention relates to a novel benzoyl cyanide derivative useful as an intermediate for agricultural and pharmaceutical products, a process for producing the same, and a reaction using the same.
【０００２】[0002]
【従来の技術】２−置換ベンゾイル−１，３−シクロヘ
キサンジオン類が除草剤として有用なことは既に知られ
ており、種々の置換基ないし骨格を有するものが提案さ
れている。2. Description of the Related Art It is already known that 2-substituted benzoyl-1,3-cyclohexanediones are useful as herbicides, and those having various substituents or skeletons have been proposed.
【０００３】[0003]
【発明が解決しようとする課題】本発明は農医薬中間体
として有用な新規なベンゾイルシアナイド誘導体、その
製法及びそれを用いた反応を提供することを目的とす
る。SUMMARY OF THE INVENTION It is an object of the present invention to provide a novel benzoyl cyanide derivative useful as an intermediate for agricultural and pharmaceutical products, a process for producing the same, and a reaction using the same.
【０００４】[0004]
【課題を解決するための手段】本発明は、式〔Ｉ〕The present invention provides a compound of formula [I]
【化１０】 〔式中、Ｒ1 はハロゲン原子またはＣ1-6 のアルキル基
を表し、Ｒ2 およびＲ3は同一または相異なってＣ1-6
のアルキル基を表し、ｍは０〜２の整数を表し、ｎは０
〜２の整数を表す。〕で表されるベンゾイルシアナイド
誘導体、その製法及びそれを用いた反応である。[Chemical 10] [In the formula, R 1 represents a halogen atom or a C 1-6 alkyl group, and R 2 and R 3 are the same or different and are C 1-6.
Represents an alkyl group, m represents an integer of 0 to 2, and n represents 0.
Represents an integer of 2; ] It is a benzoyl cyanide derivative represented by these, its manufacturing method, and the reaction using the same.
【０００５】本発明化合物は次に示す方法によって製造
される。The compound of the present invention is produced by the following method.
【化１１】 式中、Ｒ1 、Ｒ2 、Ｒ3 、ｍおよびｎは前記と同じ意味
を表し、Ｘはハロゲン原子を表す。[Chemical 11] In the formula, R 1 , R 2 , R 3 , m and n have the same meanings as described above, and X represents a halogen atom.
【０００６】 不活性溶媒中、式〔II〕で表される化
合物とシアン化物を触媒存在下に反応させる。不活性溶
媒としては、ベンゼン、トルエン等のＢＴＸ系溶媒類、
塩化メチレン、クロロホルム等のハロゲン化炭化水素類
などが挙げられる。シアン化物としては、例えば、トリ
アルキルシリルシアナイドが挙げられ、ｎ＝２のときは
トリアルキルシリルシアナイドが好ましい。触媒として
は四塩化スズ、四塩化チタン等のルイス酸などである
（参考：Ｓｙｎｔｈｅｓｉｓ，１９７９，５２３）。A compound represented by the formula [II] and cyanide are reacted in the presence of a catalyst in an inert solvent. Examples of the inert solvent include BTX-based solvents such as benzene and toluene,
Examples thereof include halogenated hydrocarbons such as methylene chloride and chloroform. Examples of cyanide include trialkylsilyl cyanide, and when n = 2, trialkylsilyl cyanide is preferable. Examples of the catalyst include Lewis acids such as tin tetrachloride and titanium tetrachloride (reference: Synthesis, 1979 , 523).
【０００７】 式〔II〕で表される化合物とシアン化
物を不活性ガス雰囲気下、１４０〜２００℃、好ましく
は１５０〜１７０℃で反応させる。シアン化物として
は、例えば、シアン化銅（Ｉ）、シアン化水銀、シアン
化銀などが挙げられ、不活性ガスとしては、例えば、窒
素ガスである（参考：Ａｎｇｅｗ．Ｃｈｅｍ．，６８，
４２５（１９５６））。The compound represented by the formula [II] and cyanide are reacted in an inert gas atmosphere at 140 to 200 ° C., preferably 150 to 170 ° C. Examples of cyanides include copper (I) cyanide, mercury cyanide, and silver cyanide, and examples of the inert gas include nitrogen gas (reference: Angew. Chem., 68 ,
425 (1956)).
【０００８】 式〔II〕で表される化合物とシアン化
物を不活性溶媒と水の混合溶媒中、相間移動触媒存在下
に反応させる。シアン化物としては、例えば、シアン化
ソーダ、シアン化カリウムなどが挙げられ、不活性溶媒
としては、ベンゼン、トルエン等のＢＴＸ系溶媒類、塩
化メチレン、クロロホルム等のハロゲン化炭化水素類な
どが挙げられ、相間移動触媒としては、相間移動触媒と
して知られているアンモニウム塩類、ホスホニウム塩
類、クラウンエーテル類などである（参考：Ｔｅｔｒａ
ｈｅｄｒｏｎ Ｌｅｔｔ．，１９７４，２２７５）。The compound represented by the formula [II] and cyanide are reacted in a mixed solvent of an inert solvent and water in the presence of a phase transfer catalyst. Examples of cyanides include sodium cyanide and potassium cyanide, and examples of the inert solvent include BTX solvents such as benzene and toluene, and halogenated hydrocarbons such as methylene chloride and chloroform. Examples of the transfer catalyst include ammonium salts, phosphonium salts, crown ethers and the like, which are known as phase transfer catalysts (reference: Tetra
hedron Lett. , 1974, 2275).
【０００９】 式〔II〕で表される化合物とシアン化
物を不活性溶媒中、相間移動触媒存在下に５０〜１００
℃、好ましくは７０〜９０℃で反応させる。シアン化物
としては、例えば、シアン化銅（Ｉ）、シアン化ソー
ダ、シアン化カリウムなどが挙げられ、不活性溶媒とし
ては、ＤＭＦ、ＤＭＳＯ、アセトニトリルなどが挙げら
れ、好ましくはアセトニトリルであり、相間移動触媒と
しては、相間移動触媒として知られているアンモニウム
塩類、ホスホニウム塩類、クラウンエーテル類などであ
る。The compound represented by the formula [II] and cyanide are mixed in an inert solvent in the presence of a phase transfer catalyst at 50 to 100%.
C., preferably 70 to 90.degree. C. Examples of the cyanide include copper (I) cyanide, sodium cyanide, potassium cyanide and the like, and the inert solvent includes DMF, DMSO, acetonitrile and the like, preferably acetonitrile, and as the phase transfer catalyst. Are ammonium salts, phosphonium salts, crown ethers, etc. which are known as phase transfer catalysts.
【００１０】式〔Ｉ〕で表される化合物は下記の反応に
より式〔III 〕で表される化合物と反応し、式〔IV〕で
表される化合物を高収率で製造することができる。The compound represented by the formula [I] is reacted with the compound represented by the formula [III] by the following reaction to produce the compound represented by the formula [IV] in high yield.
【化１２】 式中、Ｒ1 、Ｒ2 、Ｒ3 、ｍ、ｎは前記と同じ意味を表
し、Ａは置換されてもよい５〜７員の炭素環または置換
されてもよい５〜７員のＮ，ＯまたはＳを含むヘテロ環
を表す。反応は、〔Ｉ〕と〔III 〕及び塩基の当モル混
合溶液を加熱することにより行なわれる。塩基としては
例えばピリジン、トリエチルアミン、ＤＢＵなどがあげ
られる。溶媒としては塩化メチレン、クロロホルム、ア
セトニトリル、トルエンなどが用いられ、反応はこれら
の溶媒の沸点で行われる。[Chemical 12] In the formula, R 1 , R 2 , R 3 , m and n have the same meanings as described above, and A is an optionally substituted 5 to 7 membered carbocycle or an optionally substituted 5 to 7 membered N, Represents a heterocycle containing O or S. The reaction is carried out by heating an equimolar mixed solution of [I] and [III] and a base. Examples of the base include pyridine, triethylamine, DBU and the like. As the solvent, methylene chloride, chloroform, acetonitrile, toluene and the like are used, and the reaction is carried out at the boiling point of these solvents.
【００１１】式〔III 〕で表される化合物は、例えば、The compound represented by the formula [III] is, for example,
【化１３】 等である。〔ここで、Ｒ4 、Ｒ5 、Ｒ6 、Ｒ7 、Ｒ8 、
Ｒ9 は同一または相異なってハロゲン原子、置換されて
もよいアルキル基、アルコキシカルボニル基、置換され
てもよいアルケニル基、置換されてもよいフェニル基を
表し、またＲ5 とＲ6 で置換されてもよい３〜７員の炭
素環を形成してもよい。Ｒ10、Ｒ11、Ｒ12、Ｒ13は、同
一又は相異なって、水素又は低級アルキルを表す。Ｒ14
は、水素を表す。Ｒ15は、ＯＲ16を表し、Ｒ16は水素、
低級アルキル、アラルキル、低級アシル、アルキルスル
ホニル、アリールスルホニルを表し、またはＲ14とＲ15
は一緒になって単結合を表してもよい。また、Ｚは、酸
素、硫黄又はＮ−Ｒ17を表し、Ｒ17は水素、低級アルキ
ル、置換されてもよいアラルキル、置換されてもよいシ
クロアルキル、置換されてもよいフェニル、又は置換さ
れてもよい複素環を表す。[Chemical 13] Etc. [Here, R 4 , R 5 , R 6 , R 7 , R 8 ,
R 9 is the same or different and represents a halogen atom, an optionally substituted alkyl group, an alkoxycarbonyl group, an optionally substituted alkenyl group or an optionally substituted phenyl group, and is substituted by R 5 and R 6. It may form a 3- to 7-membered carbon ring. R 10 , R 11 , R 12 , and R 13 are the same or different and each represent hydrogen or lower alkyl. R 14
Represents hydrogen. R 15 represents OR 16 , R 16 is hydrogen,
Represents lower alkyl, aralkyl, lower acyl, alkylsulfonyl, arylsulfonyl, or R 14 and R 15
May together represent a single bond. Z represents oxygen, sulfur or NR 17 , and R 17 is hydrogen, lower alkyl, optionally substituted aralkyl, optionally substituted cycloalkyl, optionally substituted phenyl, or substituted. Represents a heterocycle.
【００１２】また〔IV〕においてｎ＝０である〔IV″〕
は酸化することにより高収率で〔IV′〕にすることがで
きる。Further, in [IV], n = 0, [IV ″]
Can be converted to [IV '] in high yield by oxidation.
【化１４】 式中、Ｒ1 、Ｒ2 、Ｒ3 、ｍ、Ａは前記と同じ意味を表
す。反応は、通常の酸化反応で行なわれる。例えばタン
グステン酸ナトリウムを触媒として２倍モル以上の過酸
化水素と〔IV″〕を加熱することにより行われる。溶媒
としては酢酸、水、アルコール類、又はこれらの混合溶
媒が用いられ、反応は１００℃ないしこれらの溶媒の沸
点で行われる。[Chemical 14] In the formula, R 1 , R 2 , R 3 , m and A have the same meanings as described above. The reaction is carried out by a usual oxidation reaction. For example, it is carried out by heating [IV ″] with hydrogen peroxide in an amount not less than twice the molar amount of sodium tungstate as a catalyst. Acetic acid, water, alcohols, or a mixed solvent thereof is used, and the reaction is 100 C. to the boiling point of these solvents.
【００１３】反応終了後は、通常の後処理を行うことに
より目的物を得ることができる。合成した化合物は、Ｎ
ＭＲ、ＩＲ、ＭＳ等より同定した。After completion of the reaction, the desired product can be obtained by carrying out a usual post-treatment. The synthesized compound is N
It was identified by MR, IR, MS and the like.
【００１４】尚、環Ａには下に示すような互変異性体が
存在しうる。The ring A may have tautomers as shown below.
【化１５】 [Chemical 15]
【００１５】[0015]
【実施例】次に実施例を挙げて、本発明を更に具体的に
説明する。 実施例１ ３−メトキシ−２−メチル−４−メチルチオベンゾイル
シアナイドの合成 （参考；Ｔｅｔｒａｈｅｄｒｏｎ Ｌｅｔｔ．，２６，
２２７５（１９７４））EXAMPLES Next, the present invention will be described more specifically with reference to examples. Example 1 Synthesis of 3-methoxy-2-methyl-4-methylthiobenzoyl cyanide (Reference: Tetrahedron Lett., 26 ,
2275 (1974))
【化１６】 ３−メトキシ−２−メチル−４−メチルチオ安息香酸ク
ロライド２３ｇとテトラブチルアンモニウムブロマイド
３ｇのジクロロエタン２００ｍｌ溶液に、０℃窒素気流
下で１０％シアン化ナトリウム水溶液５０ｇを１時間か
けて滴下する。１時間撹拌した後有機層を分取し、水、
飽和塩化ナトリウム水溶液で順次洗浄し、硫酸マグネシ
ウムで乾燥した。溶媒を減圧にて留去し、目的物１４．
８ｇを得た。ｍｐ１１５〜８℃。[Chemical 16] To a solution of 23 g of 3-methoxy-2-methyl-4-methylthiobenzoyl chloride and 3 g of tetrabutylammonium bromide in 200 ml of dichloroethane, 50 g of a 10% sodium cyanide aqueous solution was added dropwise over 1 hour under a nitrogen stream at 0 ° C. After stirring for 1 hour, the organic layer was separated, water,
It was washed successively with saturated aqueous sodium chloride solution and dried over magnesium sulfate. The solvent was distilled off under reduced pressure to obtain the desired product 14.
8 g was obtained. mp 115-8 ° C.
【００１６】実施例２ Ｅ−２−ヒドロキシ−５−エトキシカルボニル−３−
（３−メトキシ−２−メチル−４−メチルチオベンゾイ
ル）−５−メチル−２−ビシクロ〔４，１，０〕ヘプテ
ン−４−オンの合成Example 2 E-2-hydroxy-5-ethoxycarbonyl-3-
Synthesis of (3-methoxy-2-methyl-4-methylthiobenzoyl) -5-methyl-2-bicyclo [4,1,0] hepten-4-one
【化１７】 実施例１で得たベンゾイルシアナイド２．２ｇとＥ−２
−ヒドロキシ−５−エトキシカルボニル−５−メチル−
２−ビシクロ〔４，１，０〕ヘプテン−４−オン２．１
ｇを２０ｍｌの塩化メチレンに溶解する。この溶液にト
リエチルアミン１．２ｇを室温にて添加した。室温にて
１８時間撹拌した後、氷水にあけ濃塩酸で酸性化し有機
層を分取した。この有機層を水洗、硫酸マグネシウムで
乾燥、溶媒を減圧にて留去し、目的物３．５ｇ（Ｅ体）
を得た。ｍｐ１１１〜１１２℃（Ｅ体）[Chemical 17] 2.2 g of benzoyl cyanide obtained in Example 1 and E-2
-Hydroxy-5-ethoxycarbonyl-5-methyl-
2-bicyclo [4,1,0] hepten-4-one 2.1
g is dissolved in 20 ml of methylene chloride. To this solution was added 1.2 g of triethylamine at room temperature. After stirring at room temperature for 18 hours, the mixture was poured into ice water, acidified with concentrated hydrochloric acid, and the organic layer was separated. This organic layer was washed with water, dried over magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain 3.5 g of the desired product (E form).
Got mp111-112 ° C (E body)
【００１７】実施例３ Ｚ−２−ヒドロキシ−５−エトキシカルボニル−３−
（３−メトキシ−２−メチル−４−メチルチオベンゾイ
ル）−５−メチル−２−ビシクロ〔４，１，０〕ヘプテ
ン−４−オンの合成 ２−ヒドロキシ−５−エトキシカルボニル−５−メチル
−２−ビシクロ〔４，１，０〕ヘプテン−４−オン２．
１ｇのＥ体の代りにＺ体を用いる他は、実施例２に準じ
て反応、後処理し、アモルファスな目的物３．４ｇ（Ｚ
体）を得た。Example 3 Z-2-hydroxy-5-ethoxycarbonyl-3-
Synthesis of (3-methoxy-2-methyl-4-methylthiobenzoyl) -5-methyl-2-bicyclo [4,1,0] hepten-4-one 2-hydroxy-5-ethoxycarbonyl-5-methyl-2 -Bicyclo [4,1,0] hepten-4-one 2.
3.4 g (Z) of the target compound which was amorphous was reacted and post-treated according to Example 2 except that the Z-form was used instead of the 1-g E-form.
Got a body).
【００１８】実施例４ Ｅ−２−ヒドロキシ−５−エトキシカルボニル−３−
（４−メシル−３−メトキシ−２−メチルベンゾイル）
−５−メチル−２−ビシクロ〔４，１，０〕ヘプテン−
４−オンの合成Example 4 E-2-Hydroxy-5-ethoxycarbonyl-3-
(4-mesyl-3-methoxy-2-methylbenzoyl)
-5-methyl-2-bicyclo [4,1,0] heptene-
4-one synthesis
【化１８】 実施例２で得たビシクロ環化合物２．２ｇの２０ｍｌメ
タノール溶液にタングステン酸ナトリウム０．１６ｇを
加えたのち、３５％過酸化水素水１．７ｇを室温にて添
加した。２時間還流後希塩酸を注加し有機層を分取し
た。水洗、硫酸マグネシウムで乾燥、溶媒を減圧留去
し、目的物１．８３ｇを得た。[Chemical 18] To a solution of 2.2 g of the bicyclo ring compound obtained in Example 2 in 20 ml of methanol was added 0.16 g of sodium tungstate, and then 1.7 g of 35% hydrogen peroxide solution was added at room temperature. After refluxing for 2 hours, dilute hydrochloric acid was added to separate the organic layer. It was washed with water, dried over magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain 1.83 g of the desired product.
【００１９】実施例５ Ｚ−２−ヒドロキシ−５−エトキシカルボニル−３−
（４−メシル−３−メトキシ−２−メチルベンゾイル）
−５−メチル−２−ビシクロ〔４，１，０〕ヘプテン−
４−オンの合成 ビシクロ環化合物２．２ｇのＥ体の代りにＺ体（実施例
３で得た）を用いる他は実施例４に準じて反応、後処理
し、目的物１．９４ｇ（Ｚ）を得た。Example 5 Z-2-hydroxy-5-ethoxycarbonyl-3-
(4-mesyl-3-methoxy-2-methylbenzoyl)
-5-methyl-2-bicyclo [4,1,0] heptene-
Synthesis of 4-one The reaction and post-treatment were carried out in the same manner as in Example 4 except that the Z form (obtained in Example 3) was used in place of the E form of 2.2 g of the bicyclo ring compound, and 1.94 g (Z ) Got.
【００２０】実施例６ ２−ヒドロキシ−５−エトキシカルボニル−３−（４−
メシル−３−メトキシ−２−メチルベンゾイル−５−メ
チル−２−ビシクロ〔４，１，０〕ヘプテン−４−オン
の合成Example 6 2-Hydroxy-5-ethoxycarbonyl-3- (4-
Synthesis of mesyl-3-methoxy-2-methylbenzoyl-5-methyl-2-bicyclo [4,1,0] hepten-4-one
【化１９】 ２−メチル−４−メチルスルホニル−３−メトキシ安息
香酸クロライド２．６ｇとトリメチルシリルシアナイド
１．１ｇの塩化メチレン溶液５０ｍｌに四塩化スズ０．
２ｍｌを室温、窒素雰囲気下にて添加した。２０時間撹
拌後、反応溶液を水に注いだ。水層を分離し、有機層を
５０ｍｌの水で２回洗浄した後、乾燥濃縮して、３−メ
トキシ−２−メチル−４−メシルベンゾイルシアナイド
の粗生成物を得た。この粗生成物と２−ヒドロキシ−５
−エトキシカルボニル−５−メチル−２−ビシクロ
〔４，１，０〕ヘプテン−４−オン１．２ｇの２０ｍｌ
塩化メチレン溶液にトリエチルアミン０．９ｍｌを加え
た。５時間反応混合物を室温で撹拌したのち、１規定塩
酸に注いだ。水層を分離し、有機層を飽和食塩水で洗浄
した。乾燥濃縮後、シリカゲルカラムクロマトグラフィ
ー（溶出液：ヘキサン−酢酸エチル）で精製して目的化
合物１．２ｇを得た。[Chemical 19] A solution of 2.6 g of 2-methyl-4-methylsulfonyl-3-methoxybenzoic acid chloride and 1.1 g of trimethylsilyl cyanide in 50 ml of methylene chloride was added to 0.4 ml of tin tetrachloride.
2 ml was added at room temperature under a nitrogen atmosphere. After stirring for 20 hours, the reaction solution was poured into water. The aqueous layer was separated, the organic layer was washed twice with 50 ml of water, and then dried and concentrated to obtain a crude product of 3-methoxy-2-methyl-4-mesylbenzoyl cyanide. This crude product and 2-hydroxy-5
-Ethoxycarbonyl-5-methyl-2-bicyclo [4,1,0] hepten-4-one 1.2 g 20 ml
0.9 ml of triethylamine was added to the methylene chloride solution. The reaction mixture was stirred at room temperature for 5 hours and then poured into 1N hydrochloric acid. The aqueous layer was separated and the organic layer was washed with saturated brine. After drying and concentration, the residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate) to obtain 1.2 g of the target compound.
【００２１】[0021]
【発明の効果】本発明化合物は農医薬中間体として有用
である。本発明化合物を用いれば、例えば、特開平２−
７２６、Ｗ０９１／００２６０、特願平３−１９３５９
５、特願平４−２０３２４１に示される除草剤を工業的
に有利に製造することができる。The compound of the present invention is useful as an intermediate for agricultural medicine. When the compound of the present invention is used, for example, JP-A-2-
726, W091 / 00260, Japanese Patent Application No. 3-19359
5, the herbicide disclosed in Japanese Patent Application No. 4-203241 can be industrially advantageously produced.
Claims (4)
を表し、Ｒ2 およびＲ3は同一または相異なってＣ1-6
のアルキル基を表し、ｍは０〜２の整数を表し、ｎは０
〜２の整数を表す。〕で表される化合物。1. A compound represented by the formula [I]: [In the formula, R 1 represents a halogen atom or a C 1-6 alkyl group, and R 2 and R 3 are the same or different and are C 1-6.
Represents an alkyl group, m represents an integer of 0 to 2, and n represents 0.
Represents an integer of 2; ] The compound represented by these.
味を表す。〕で表される化合物とシアン化物を反応させ
ることを特徴とする式〔Ｉ〕 【化３】 〔式中、Ｒ1 、Ｒ2 、Ｒ3 、ｍ、ｎは前記と同じ意味を
表す。〕で表される化合物の製法。2. A formula [II]: [In the formula, R 1 , R 2 , R 3 , m and n have the same meanings as described above. ] The compound represented by the formula [I] [In the formula, R 1 , R 2 , R 3 , m and n have the same meanings as described above. ] The manufacturing method of the compound represented by these.
味を表す。〕で表される化合物と式〔III 〕 【化５】 〔式中、Ａは置換されてもよい５〜７員の炭素環または
置換されてもよい５〜７員のＮ、ＯもしくはＳを含む複
素環を表す。〕で表される化合物を反応させることを特
徴とする式〔IV〕 【化６】 〔式中、Ｒ1 、Ｒ2 、Ｒ3 、ｍ、ｎおよびＡは前記と同
じ意味を表す。〕で表される化合物の製法。3. The formula [I]: [In the formula, R 1 , R 2 , R 3 , m and n have the same meanings as described above. ] And a compound of formula [III] [In the formula, A represents an optionally substituted 5 to 7-membered carbon ring or an optionally substituted 5 to 7-membered heterocyclic ring containing N, O or S. ] The compound represented by the formula [IV] [In the formula, R 1 , R 2 , R 3 , m, n and A have the same meanings as described above. ] The manufacturing method of the compound represented by these.
表す。〕で表される化合物と式〔III 〕 【化８】 〔式中、Ａは前記と同じ意味を表す。〕で表される化合
物を反応させ、次いで酸化することを特徴とする式〔I
V′〕 【化９】 〔式中、Ｒ1 、Ｒ2 、Ｒ3 、ｍおよびＡは前記と同じ意
味を表す。〕で表される化合物の製法。4. A compound represented by the formula [I ′]: [In the formula, R 1 , R 2 , R 3 and m have the same meanings as described above. ] And a compound of formula [III] [In formula, A represents the same meaning as the above. ] The compound represented by the formula [I
V '] [In the formula, R 1 , R 2 , R 3 , m and A have the same meanings as described above. ] The manufacturing method of the compound represented by these.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2363693A JPH06211780A (en) | 1993-01-19 | 1993-01-19 | Benzoyl cyanide derivative, its production and reaction using the same |
| PCT/JP1993/000414 WO1993020035A1 (en) | 1992-04-03 | 1993-04-01 | Process for producing cyclopropane derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2363693A JPH06211780A (en) | 1993-01-19 | 1993-01-19 | Benzoyl cyanide derivative, its production and reaction using the same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH06211780A true JPH06211780A (en) | 1994-08-02 |
Family
ID=12116067
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2363693A Pending JPH06211780A (en) | 1992-04-03 | 1993-01-19 | Benzoyl cyanide derivative, its production and reaction using the same |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH06211780A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SG79243A1 (en) * | 1997-12-17 | 2001-03-20 | Ciba Sc Holding Ag | Process for ink-jet printing textile fibre materials |
| KR102032053B1 (en) * | 2018-04-13 | 2019-10-14 | 전북대학교산학협력단 | Composition for insecticide or acaricide containing cyanide derivatives or salt thereof |
-
1993
- 1993-01-19 JP JP2363693A patent/JPH06211780A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SG79243A1 (en) * | 1997-12-17 | 2001-03-20 | Ciba Sc Holding Ag | Process for ink-jet printing textile fibre materials |
| KR102032053B1 (en) * | 2018-04-13 | 2019-10-14 | 전북대학교산학협력단 | Composition for insecticide or acaricide containing cyanide derivatives or salt thereof |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EA002427B1 (en) | Process for making dirylpyridines useful as cox-2 inhibitors | |
| JP2575781B2 (en) | 2,3-diacyloxy-4-hydroxy-topenanal and method for producing the same | |
| JPH06211780A (en) | Benzoyl cyanide derivative, its production and reaction using the same | |
| WO1985000037A1 (en) | 4-chloro-4-methyl-5-methylene-1,3-dioxolan-2-one | |
| JP2599610B2 (en) | Process for producing 2β-substituted methylpenicillin derivatives | |
| JPH0141152B2 (en) | ||
| JPH05286894A (en) | New production of carboxylic acid ester or carboxylic acid thioster | |
| JPH037245A (en) | Preparation of 2-oxo-3-aromatic carboxylic acid derivative | |
| JPH0798795B2 (en) | Sulfonamide-substituted unsaturated fatty acid | |
| JP3231207B2 (en) | Method for producing sulfenylacetic acid derivative | |
| JPS6019312B2 (en) | Method for producing oxazolinoazetidinylpentenoic acid derivatives | |
| JP3233806B2 (en) | Method for producing sulfenylacetic acid derivative | |
| JPH03236343A (en) | Production of dialdehyde derivative | |
| JPH10287657A (en) | Production of radiosensitizer | |
| JPH01294661A (en) | Production of 4-acetoxyazetidinone derivative | |
| KR0157511B1 (en) | Process for the preparation of 2-sulfonylthiazole carboxamide derivatives | |
| JPH07247263A (en) | Production of methylthiobenzene compound | |
| JP2501604B2 (en) | Process for producing cholesta-1,4,6-trien-3-ones | |
| JPH0812658A (en) | Production of sydnones | |
| JPH01168673A (en) | Production of 1,3-dialkylpyrazole-4-aldehydes | |
| JPH05213922A (en) | New process for producing lactone derivative | |
| JPH08176134A (en) | New synthetic method of phthalide derivative | |
| JPH0324077A (en) | Production of imidazole derivative | |
| JPH07133271A (en) | Banzaldehyde derivative and production of chromancarboxylic acid derivative using the same as intermediate | |
| JPS606951B2 (en) | Lactone production method |