JPH04173786A - Production of 4-keto-tetrahydro-'-carboline compound - Google Patents
Production of 4-keto-tetrahydro-'-carboline compoundInfo
- Publication number
- JPH04173786A JPH04173786A JP2300562A JP30056290A JPH04173786A JP H04173786 A JPH04173786 A JP H04173786A JP 2300562 A JP2300562 A JP 2300562A JP 30056290 A JP30056290 A JP 30056290A JP H04173786 A JPH04173786 A JP H04173786A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- indole
- compound
- tetrahydro
- keto
- 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
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 150000001875 compounds Chemical class 0.000 title abstract description 4
- -1 indole compound Chemical class 0.000 claims abstract description 23
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- SIKJAQJRHWYJAI-UHFFFAOYSA-N benzopyrrole Natural products C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims abstract description 6
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims abstract description 6
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000003377 acid catalyst Substances 0.000 claims abstract description 5
- 238000003756 stirring Methods 0.000 claims abstract description 4
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims abstract description 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims abstract description 3
- 238000010438 heat treatment Methods 0.000 claims abstract 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims 2
- 229920000137 polyphosphoric acid Polymers 0.000 abstract description 5
- HCUARRIEZVDMPT-UHFFFAOYSA-N Indole-2-carboxylic acid Chemical compound C1=CC=C2NC(C(=O)O)=CC2=C1 HCUARRIEZVDMPT-UHFFFAOYSA-N 0.000 abstract description 4
- KZNYDMSDPPSZCG-UHFFFAOYSA-N 1,2,3,4a-tetrahydropyrido[3,4-b]indol-4-one Chemical compound C1=CC=C2C3C(=O)CNCC3=NC2=C1 KZNYDMSDPPSZCG-UHFFFAOYSA-N 0.000 abstract description 3
- SBNOTUDDIXOFSN-UHFFFAOYSA-N 1h-indole-2-carbaldehyde Chemical compound C1=CC=C2NC(C=O)=CC2=C1 SBNOTUDDIXOFSN-UHFFFAOYSA-N 0.000 abstract description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Natural products NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 abstract description 2
- 239000004471 Glycine Substances 0.000 abstract description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 abstract description 2
- 239000003814 drug Substances 0.000 abstract description 2
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 abstract description 2
- 230000001590 oxidative effect Effects 0.000 abstract description 2
- 239000002994 raw material Substances 0.000 abstract description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 abstract 2
- 239000005445 natural material Substances 0.000 abstract 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 238000000034 method Methods 0.000 description 6
- 239000013078 crystal Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- AIFRHYZBTHREPW-UHFFFAOYSA-N β-carboline Chemical compound N1=CC=C2C3=CC=CC=C3NC2=C1 AIFRHYZBTHREPW-UHFFFAOYSA-N 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 125000001041 indolyl group Chemical group 0.000 description 2
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- RNAODKZCUVVPEN-UHFFFAOYSA-N 1h-indol-2-ylmethanamine Chemical class C1=CC=C2NC(CN)=CC2=C1 RNAODKZCUVVPEN-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 238000004896 high resolution mass spectrometry Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- JXDYKVIHCLTXOP-UHFFFAOYSA-N isatin Chemical compound C1=CC=C2C(=O)C(=O)NC2=C1 JXDYKVIHCLTXOP-UHFFFAOYSA-N 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- ZXLDQJLIBNPEFJ-UHFFFAOYSA-N tetrahydro-beta-carboline Natural products C1CNC(C)C2=C1C1=CC=C(OC)C=C1N2 ZXLDQJLIBNPEFJ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
【発明の詳細な説明】
［産業上の利用分野コ
本発明は、医薬品や生理活性のある天然物の合成に有用
な中間体である４−ケト−テトラハイドロ−β−カルボ
リン化合物の製造方法に関するものである。Detailed Description of the Invention [Field of Industrial Application] The present invention relates to a method for producing a 4-keto-tetrahydro-β-carboline compound, which is an intermediate useful in the synthesis of pharmaceuticals and physiologically active natural products. It is something.
［従来の技術］
４−ケト−テトラハイドロ−β−カルボリン化合物の製
造方法としては、タック等によるテトラハイドロ−β−
カルボリンに対するＤＤＱによる酸化の方法が知られて
いる。（Ｊ、Ｍ、Ｃｏｏｋ、ｅｔ ａｌ。[Prior art] As a method for producing a 4-keto-tetrahydro-β-carboline compound, tetrahydro-β-carboline compound by tack etc.
A method of oxidizing carboline with DDQ is known. (J.M.Cook, et al.
Ｊ、Ｏｒｇ、Ｃｈｅｍ、、４７．４９３３．（１９８２
）） Ｌがし、この方法は高価な試薬を使うことや目
的物の収率の再現性が良くないことなどの点で良い方法
とは言えない。また、ジョンソン等は、インドール−２
−力ルボン酸アミド誘導体を濃硫酸で環化する方法を試
みているが、インドール環の窒素への閉環反応が優先し
、β−カルボリンは少量しか得られていない、 （Ｊ
、Ｒ，Ｊｏｈｎｓｏｎ、ｅｔ ａｌ、Ｊ、Ａｍ、Ｃｈｅ
ｍ、Ｓｏｃ、、５９゜２３６４ 、 （１９４７） ）
本発明者等は先に、インドール環の窒素をベンジル
基で保護したインドール−２＝力ルボン酸誘導体を環化
してβ−カルボリン化合物を合成する研究を報告した。J,Org,Chem,, 47.4933. (1982
)) However, this method cannot be said to be a good method because it uses expensive reagents and the reproducibility of the yield of the target product is poor. Also, Johnson et al.
- A method of cyclizing carboxylic acid amide derivatives with concentrated sulfuric acid has been attempted, but the ring-closing reaction to the nitrogen of the indole ring takes precedence, and only a small amount of β-carboline is obtained. (J
, R. Johnson, et al., J. Am., Che.
m, Soc, 59°2364, (1947))
The present inventors previously reported a study in which a β-carboline compound was synthesized by cyclizing an indole-2=carboxylic acid derivative in which the nitrogen of the indole ring was protected with a benzyl group.
（Ｙ、Ｍｕｒａｋａｍｉ。(Y, Murakami.
ｅｔ ａｔ、Ｈｅｔｅｒｏｃｙｃｌｅｓ、２６，８７５
．（１９８７）） Ｌかし、最終合成段階での保護基
の脱離反応が難しく、必ずしも満足できる方法ではなか
った。et at, Heterocycles, 26,875
．． (1987)) However, the removal reaction of the protecting group in the final synthesis step was difficult, and the method was not necessarily satisfactory.
［発明が解決しようとする課題］
本発明は、簡便で収率の良い４−ケト−テトラハイドロ
−β−カルボリン化合物の新規な製造方法を提供するこ
とを目的とする。[Problems to be Solved by the Invention] An object of the present invention is to provide a novel method for producing a 4-keto-tetrahydro-β-carboline compound that is simple and has a high yield.
［課題を解決するための手段］
すなわち本発明は、−綴代（Ｉ＞
（式中、Ｒ１は水素原子又は低級アルキル基を表し、Ｒ
２は水素原子、ホルミル基及びベンゾイル基から選ばれ
る１種を表し、Ｒ３は低級アルキル基を表す。〉
で示されるインドール化合物を酸触媒の存在下に加熱攪
拌することを特徴とする
一般式（ＩＩ）
（式中、Ｒ１及びＲ２は前記に同じ。）で示される４−
ケト−テトラハイドロ−β−カルボリン化合物の製造方
法である。[Means for Solving the Problems] That is, the present invention provides -sujiration (I> (wherein, R1 represents a hydrogen atom or a lower alkyl group, and R1 represents a hydrogen atom or a lower alkyl group,
2 represents one selected from a hydrogen atom, a formyl group, and a benzoyl group, and R3 represents a lower alkyl group. 〉 The indole compound represented by the general formula (II) (wherein R1 and R2 are the same as above) is heated and stirred in the presence of an acid catalyst.
This is a method for producing a keto-tetrahydro-β-carboline compound.
本発明の出発物質である一般式（Ｉ）で示されるインド
ール化合物は、例えば、次面のような方法で合成できる
。The indole compound represented by the general formula (I), which is the starting material of the present invention, can be synthesized, for example, by the following method.
インドール−２−カルボン酸をリチウムアルミニウムハ
イドライドで還元し、アルコール体とした後、二酸化マ
ンガンで酸化してインドール−２−アルデヒドとする。Indole-2-carboxylic acid is reduced with lithium aluminum hydride to form an alcohol, and then oxidized with manganese dioxide to form indole-2-aldehyde.
これにトリエチルアミンの存在下グリシンエステルを反
応させ、ソジウムボロシアノハイドライドで還元してア
ミノメチルインドール誘導体を得る。これをそのまま、
或はギ酸エチルやベンゾイルクロライドと反応させて一
般式（Ｉ）の化合物に導くことができる。This is reacted with glycine ester in the presence of triethylamine and reduced with sodium borocyanohydride to obtain an aminomethylindole derivative. Leave this as is,
Alternatively, the compound of general formula (I) can be obtained by reacting with ethyl formate or benzoyl chloride.
本発明で得られる化合物は、−綴代（Ｉｆ）で示される
４−ケト−テトラハイドロ−β−カルボリン化合物であ
る。具体的に列挙すれば、４−ケト−テトラハイドロ−
β−カルボリン、２−ホルミル−４−ケト−テトラハイ
ドロ−β−カルボリン。The compound obtained according to the present invention is a 4-keto-tetrahydro-β-carboline compound represented by the symbol (If). Specifically, 4-keto-tetrahydro-
β-carboline, 2-formyl-4-keto-tetrahydro-β-carboline.
２−ベンゾイル−４−ケト−テトラハイドロ−β−カル
ボリン、１−エチル−２−ホルミル−４−ケト−テトラ
ハイドロ−β−カルボリン、１−エチル−２−ベンゾイ
ル−４−ケト−テトラハイドロ−β−カルボリンなどが
挙げられる。2-benzoyl-4-keto-tetrahydro-β-carboline, 1-ethyl-2-formyl-4-keto-tetrahydro-β-carboline, 1-ethyl-2-benzoyl-4-keto-tetrahydro-β -Carboline and the like.
本発明で使用される酸触媒としては、ポリリン酸又はｐ
−）ルエンスルホン酸が使用できる。The acid catalyst used in the present invention is polyphosphoric acid or p
-) Luenesulfonic acid can be used.
本発明の一実施態様を述べれば、原料（Ｉ）に約１０倍
量のポリリン酸を加えて、フラスコ中で６０℃〜８０℃
に加熱しながら強制的に攪拌して反応させる０反応終了
後、多量の水を加えて余剰のポリリン酸を分解し、目的
物を酢酸エチルで抽出し、重曹水で洗浄する。脱水、脱
溶媒などを常法によって行った後、カラムクロマトによ
って目的とする４−ケト−テトラハイドロ−β−カルボ
リン化合物を得ることができる。In one embodiment of the present invention, about 10 times the amount of polyphosphoric acid is added to the raw material (I), and the mixture is heated at 60°C to 80°C in a flask.
After the reaction is completed, a large amount of water is added to decompose the excess polyphosphoric acid, and the target product is extracted with ethyl acetate and washed with aqueous sodium bicarbonate. After dehydration, solvent removal, etc. are carried out by conventional methods, the desired 4-keto-tetrahydro-β-carboline compound can be obtained by column chromatography.
以下、実施例により本発明を更に詳細に説明する。Hereinafter, the present invention will be explained in more detail with reference to Examples.
実施例 Ｉ
Ｎ−（インドール−２−イル）メチル−Ｎ−ホルミルア
ミノ酢酸・エチルエステル３．６９０ｇ（１４，２ｍｍ
ｏｌ ）にポリリン酸３７．７７ｇを加え、８０℃で１
時間１０分強制攪拌装置にて攪拌した。反応終了後水に
あけ、酢酸エチルで抽出した。酢酸エチル相は、飽和重
曹水、飽和食塩水で洗浄し、無水硫酸マグネシウムで脱
水しな。溶媒をほとんど留去し、析出した結晶を濾過す
ると淡黄色の結晶１．４５１ｇ （収率４７．８％）を
得た。一方、母液よりメタノール−クロロホルムで再結
晶を行って、淡黄色の結晶０．３４６ｇ （収率１１．
４％）を得た。更にその母液においてシリカゲルカラム
クロマトグラフィー（展開溶媒 クロロホルム：メタノ
ール−３０：１）を行って褐色結晶０．２３９ｇ （収
率７．９％）を得た。三つの結晶を合わせると、目的物
である２−ホルミル−４−ケト−テトラハイドロ−β−
カルボリンの収率は６７．１％であった。Example I N-(indol-2-yl)methyl-N-formylaminoacetic acid ethyl ester 3.690 g (14.2 mm
Add 37.77 g of polyphosphoric acid to
The mixture was stirred for 10 minutes using a forced stirring device. After the reaction was completed, it was poured into water and extracted with ethyl acetate. Wash the ethyl acetate phase with saturated aqueous sodium bicarbonate and saturated brine, and dehydrate over anhydrous magnesium sulfate. Most of the solvent was distilled off, and the precipitated crystals were filtered to obtain 1.451 g of pale yellow crystals (yield: 47.8%). On the other hand, the mother liquor was recrystallized with methanol-chloroform to produce 0.346 g of pale yellow crystals (yield 11.
4%). Furthermore, the mother liquor was subjected to silica gel column chromatography (developing solvent: chloroform:methanol-30:1) to obtain 0.239 g (yield: 7.9%) of brown crystals. When the three crystals are combined, the target product, 2-formyl-4-keto-tetrahydro-β-
The yield of carboline was 67.1%.
分析の結果は下記のとうりであり、目的物に相違ないこ
とが確認された。The results of the analysis were as shown below, and it was confirmed that this was the target product.
・融点 ２２４〜２２５℃
−ＩＲｌ／ＭＡＸ （Ｎｕｊｏｌ） ｃｍ−’：３
２００ （ＮＨ） 、 １６６０ 、１６４０ （Ｃ＝
０ ）・Ｎ Ｍ Ｒ（ＤＭＳＯ−ｄ６） δｐｐｍ
：４．２０（２Ｈ，ｓ、Ｃｔ−Ｈ）、 ４．９０．４．
９４（２）１．ｓ。・Melting point 224-225℃ -IRl/MAX (Nujol) cm-': 3
200 (NH), 1660, 1640 (C=
0)・NMR(DMSO-d6) δppm
:4.20(2H,s,Ct-H), 4.90.4.
94(2)1. s.
Ｃ３−Ｈ）、 ７．００〜７．６０（３）１．ｍ、Ａｒ
−Ｈ）７．７５〜８．０５（ＩＨ，ｍ、Ｃ３−Ｈ）８．
１５，８．２４（ＩＨ，ｓ、−ＣＨｏ）１２．２０（Ｉ
Ｈ，ｂｒ ｓ、−ＮＨ）・ＨＲ−ＭＳ 実測値
２１４．０７４０（計算値 ２１４．０８５２＞
［発明の効果］
本発明により、今まで困難であっな４−ケト−テトラハ
イドロ−β−カルボリン化合物の合成が容易になり、好
収率を得ることができる。C3-H), 7.00-7.60 (3) 1. m, Ar
-H) 7.75-8.05 (IH, m, C3-H)8.
15,8.24(IH,s,-CHO)12.20(I
H, br s, -NH)・HR-MS actual measurement value
214.0740 (calculated value 214.0852> [Effect of the invention] The present invention facilitates the synthesis of 4-keto-tetrahydro-β-carboline compounds, which has been difficult until now, and makes it possible to obtain good yields. can.
Claims (1)
Ｒ＾２は水素原子、ホルミル基及びベンゾイル基から選
ばれる１種を表し、Ｒ＾３は低級アルキル基を表す。） で示されるインドール化合物を酸触媒の存在下に加熱攪
拌することを特徴とする 一般式（II） ▲数式、化学式、表等があります▼（II） （式中、Ｒ＾１及びＲ＾２は前記に同じ。）で示される
４−ケト−テトラハイドロ−β−カルボリン化合物の製
造方法。[Claims] 1. General formula (I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) (In the formula, R^1 represents a hydrogen atom or a lower alkyl group,
R^2 represents one selected from a hydrogen atom, a formyl group, and a benzoyl group, and R^3 represents a lower alkyl group. ) General formula (II) characterized by heating and stirring an indole compound shown in the presence of an acid catalyst ▲There are mathematical formulas, chemical formulas, tables, etc.▼(II) (In the formula, R^1 and R^2 is the same as above.) A method for producing a 4-keto-tetrahydro-β-carboline compound.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2300562A JPH04173786A (en) | 1990-11-06 | 1990-11-06 | Production of 4-keto-tetrahydro-'-carboline compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2300562A JPH04173786A (en) | 1990-11-06 | 1990-11-06 | Production of 4-keto-tetrahydro-'-carboline compound |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH04173786A true JPH04173786A (en) | 1992-06-22 |
Family
ID=17886328
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2300562A Pending JPH04173786A (en) | 1990-11-06 | 1990-11-06 | Production of 4-keto-tetrahydro-'-carboline compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH04173786A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100476359B1 (en) * | 2000-08-31 | 2005-03-16 | 주식회사한국신약 | Novel compounds as a intermediated compound for the preparation of benzastatin derivatives, and the process for the preparation |
-
1990
- 1990-11-06 JP JP2300562A patent/JPH04173786A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100476359B1 (en) * | 2000-08-31 | 2005-03-16 | 주식회사한국신약 | Novel compounds as a intermediated compound for the preparation of benzastatin derivatives, and the process for the preparation |
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