JPH064626B2 - Intermediate of lysergic acid derivative - Google Patents
Intermediate of lysergic acid derivativeInfo
- Publication number
- JPH064626B2 JPH064626B2 JP3657291A JP3657291A JPH064626B2 JP H064626 B2 JPH064626 B2 JP H064626B2 JP 3657291 A JP3657291 A JP 3657291A JP 3657291 A JP3657291 A JP 3657291A JP H064626 B2 JPH064626 B2 JP H064626B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- acid derivative
- lysergic acid
- formula
- indole
- 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.)
- Expired - Lifetime
Links
Landscapes
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Description
【０００１】本発明は、一般式The present invention has the general formula
【化２】 （式中Ｒは置換基を有していてもよいアルキル基または
アリール基、Ｒ1 は低級アルキル基を示す）で表わされ
るリゼルギン酸誘導体の中間体に関する。[Chemical 2] (Wherein R represents an alkyl group or aryl group which may have a substituent, and R 1 represents a lower alkyl group), and a lysergic acid derivative intermediate.
【０００２】式Ｉの中間体すなわち１−アシル−４−
（Ｎ−アルキル−フランカルボキシアミド）−１，２，
２ａ，３−テトラハイドロベンゾ〔ｃｄ〕インドール誘
導体は、種々の生理活性を有する麦角アルカロイドの基
体であるリゼルギン酸誘導体の合成用中間体として有用
である。Intermediate of formula I: 1-acyl-4-
(N-alkyl-furancarboxamide) -1,2,
The 2a, 3-tetrahydrobenzo [cd] indole derivative is useful as an intermediate for the synthesis of a lysergic acid derivative, which is a substrate of ergot alkaloids having various physiological activities.
【０００３】式Ｉの化合物は、一般式The compounds of formula I have the general formula
【化３】 （式中Ｒは前記の意味を有する）で表わされる１−アシ
ル−４−ケト−１，２，２ａ，３，４，５−ヘキサハイ
ドロベンゾ〔ｃｄ〕インドールをモノアルキルアミンと
反応させ、生成する一般式[Chemical 3] 1-acyl-4-keto-1,2,2a, 3,4,5-hexahydrobenzo [cd] indole represented by the formula (wherein R has the above-mentioned meaning) is reacted with a monoalkylamine to produce General formula
【化４】 （式中Ｒ及びＲ1 は前記の意味を有する）で表わされる
１−アシル−４−アルキルイミノ−１，２，２ａ，３，
４，５−ヘキサハイドロベンゾ〔ｃｄ〕インドールを、
一般式[Chemical 4] 1-acyl-4-alkylimino-1,2,2a, 3, represented by the formula: wherein R and R 1 have the above meanings.
4,5-hexahydrobenzo [cd] indole
General formula
【化５】 （式中Ｘは水酸基、ハロゲン原子、ジアルキルアミノ
基、アルコキシ基又はフリルカルボニルオキシ基を示
す）で表わされる化合物と反応させることにより得られ
る。[Chemical 5] (Wherein X represents a hydroxyl group, a halogen atom, a dialkylamino group, an alkoxy group or a furylcarbonyloxy group).
【０００４】式Ｉ、II及びIIIの化合物の置換基Ｒのた
めのアルキル基としては、メチル基、エチル基、プロピ
ル基、ブチル基等が好ましい。またＲのためのアリール
基としてはフエニル基、ナフチル基、トリル基等があげ
られる。式Ｉ及びIII の化合物の置換基Ｒ1 のための低
級アルキル基としては、メチル基、エチル基、プロピル
基、ブチル基等があげられる。The alkyl group for the substituent R in the compounds of the formulas I, II and III is preferably a methyl group, an ethyl group, a propyl group, a butyl group or the like. Examples of the aryl group for R include a phenyl group, a naphthyl group and a tolyl group. Examples of the lower alkyl group for the substituent R 1 of the compounds of the formulas I and III include a methyl group, an ethyl group, a propyl group, a butyl group and the like.
【０００５】式IIの化合物とモノアルキルアミンの反応
は常法により行うことができる。式III の化合物と式IV
の化合物の反応は溶媒中で縮合剤例えばトリエチルアミ
ンの存在下に行うことが好ましい。溶媒としてはベンゼ
ン、トルエンなどの有機溶媒が用いられる。生成物
（Ｉ）は常法により、再結晶、カラムクロマトグラフイ
などの方法で単離、精製することができる。The reaction of the compound of formula II with the monoalkylamine can be carried out by a conventional method. Compounds of formula III and formula IV
The reaction of the compound (1) is preferably carried out in a solvent in the presence of a condensing agent such as triethylamine. Organic solvents such as benzene and toluene are used as the solvent. The product (I) can be isolated and purified by a conventional method such as recrystallization and column chromatography.
【０００６】本発明の化合物を水素化硼素ナトリウムの
存在下に光照射することにより、麦角アルカロイドの基
体であるリゼルギン酸と類以の化学構造を有する８−ア
シル−３ａ，５ａ, ６ａ, ７，１１ｂ，１１ｃ−ヘキサ
ハイドロ−５−アルキル−６Ｈ−フラン〔３，２ｃ〕イ
ンドール〔４，３−fg〕−４（５Ｈ）−オン誘導体が得
られる。この化合物を用い、数工程の操作により、一般
式By irradiating the compound of the present invention with light in the presence of sodium borohydride, 8-acyl-3a, 5a, 6a, 7, which has a chemical structure similar to that of lysergic acid which is a base of ergot alkaloids, An 11b, 11c-hexahydro-5-alkyl-6H-furan [3,2c] indole [4,3-fg] -4 (5H) -one derivative is obtained. Using this compound, the general formula
【化６】 （式中Ｒ1 は前記の意味を有する）で表わされるリゼル
ギン酸誘導体を製造することができる（特開昭５９−５
３４８５号公報参照）。[Chemical 6] A lysergic acid derivative represented by the formula (wherein R 1 has the above-mentioned meaning) can be produced (JP-A-59-5).
3485 gazette).
【０００７】[0007]
【実施例】１−ベンゾイル−４−ケト−１，２，２ａ，
３，４，５−ヘキサハイドロベンゾ〔ｃｄ〕インドール
２ｇを常法により処理してイミン体を得る。このイミン
体をベンゼン２００mlに溶解したのち、トリエチルアミ
ン１ｇを加える。この溶液に、新たに製したフランカル
ボン酸クロリド１．１３ｇの無水ベンゼン溶液３０mlを
氷冷攪拌下に滴加する。滴加終了後、２時間おだやかに
還流加熱する。反応終了後、反応液を水洗し、乾燥した
のち、溶媒を留去すると、粗生成物３．２１ｇが得られ
る。これをカラムクロマトグラフイ（ＳｉＯ2 −ＣＨＣ
ｌ3 ）により精製し、エーテル−メタノールより結晶化
すると、１−ベンゾイル−４−（Ｎ−メチル−３−フラ
ンカルボキシアミド）−１，２，２ａ，３−テトラハイ
ドロベンゾ〔ｃｄ〕インドール２．６６ｇ（収率９６
％）が得られる。融点：１２８〜１３０℃（エーテル、
メタノール）。EXAMPLES 1-Benzoyl-4-keto-1,2,2a,
2 g of 3,4,5-hexahydrobenzo [cd] indole is treated by a conventional method to obtain an imine compound. After dissolving the imine product in 200 ml of benzene, 1 g of triethylamine was added. To this solution, 30 ml of a solution of freshly prepared furancarboxylic acid chloride (1.33 g) in anhydrous benzene is added dropwise with stirring under ice cooling. After the completion of the dropwise addition, the mixture is heated under gentle reflux for 2 hours. After completion of the reaction, the reaction solution is washed with water and dried, and then the solvent is distilled off to obtain 3.21 g of a crude product. This was subjected to column chromatography (SiO 2 -CHC
Purification by l 3), ether - Crystallization from methanol, 1-benzoyl-4-(N-methyl-3-furan carboxamido) -1,2,2a, 3- tetrahydro-benzo [cd] indole 2. 66 g (yield 96
%) Is obtained. Melting point: 128-130 ° C (ether,
methanol).
Claims (1)
アリール基、Ｒ1 は低級アルキル基を示す）で表わされ
るリゼルギン酸誘導体の中間体。1. A general formula: An intermediate of a lysergic acid derivative represented by the formula (wherein R is an alkyl or aryl group which may have a substituent and R 1 is a lower alkyl group).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3657291A JPH064626B2 (en) | 1991-02-07 | 1991-02-07 | Intermediate of lysergic acid derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3657291A JPH064626B2 (en) | 1991-02-07 | 1991-02-07 | Intermediate of lysergic acid derivative |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP16160082A Division JPS5953485A (en) | 1982-09-18 | 1982-09-18 | Compound related to lysergic acid and its preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH05213942A JPH05213942A (en) | 1993-08-24 |
| JPH064626B2 true JPH064626B2 (en) | 1994-01-19 |
Family
ID=12473487
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3657291A Expired - Lifetime JPH064626B2 (en) | 1991-02-07 | 1991-02-07 | Intermediate of lysergic acid derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH064626B2 (en) |
-
1991
- 1991-02-07 JP JP3657291A patent/JPH064626B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPH05213942A (en) | 1993-08-24 |
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