GB841225A - Novel quinolizine derivatives and process for the manufacture of same - Google Patents
Novel quinolizine derivatives and process for the manufacture of sameInfo
- Publication number
- GB841225A GB841225A GB28765/57A GB2876557A GB841225A GB 841225 A GB841225 A GB 841225A GB 28765/57 A GB28765/57 A GB 28765/57A GB 2876557 A GB2876557 A GB 2876557A GB 841225 A GB841225 A GB 841225A
- Authority
- GB
- United Kingdom
- Prior art keywords
- quinolizine
- give
- indolo
- octahydro
- acid
- 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
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
The invention comprises compounds of the formula <FORM:0841225/IV(b)/1> (wherein the alkyl, alkoxy and halogeno substituents are optional and R is hydrogen or an acyl group) and acid-addition salts thereof; and their preparation by reduction of the corresponding ketones by known methods and acylation of the alcohol products if desired. The reduction may be carried out by catalytic hydrogenation, by treatment with lithium aluminium hydride in an anhydrous solvent or by treatment with sodium or potassium boron hydride in methanol. The acylation may be effected with the appropriate acid anhydride in presence of a tertiary base such as pyridine or with a lower alkyl ester of the acylating acid in presence of an alkaline catalyst. Examples describe the preparation of (1) 2-hydroxy-1:2:3:4:6:7:12:12b - octahydro - indolo [2,3 - a]quinolizine and the corresponding acetoxy, butyroxy and benzoyloxy compounds therefrom; 2 - hydroxy - 3 - methyl - 1:2:3:4: 6:7:12:12b - octahydro - indolo[2,3 - a]quinolizine; (3) 2 - hydroxy - 9 - chloro - 1:2:3:4: 6:7:12:12b - octahydro - indolo[2,3 - a]quinolizine by condensing 5-chloro-tryptamine with ethoxycarbonyl-pyruvic acid and esterifying the product with ethanolic hydrochloric acid to give ethyl 6 - chloro - 2:3:4:9 - tetrahydro-1H - pyrid[3,4 - b]indole - 1 - acetate hydrochloride, converting this to the free base and heating with ethyl acrylate to give a crude product, heating this with sodium ethoxide in benzene to give a crude b -keto ester, heating this with hydrochloric acid to give 2-oxo-9-chloro - 1:2:3:4:6:7:12:12b - octahydroindolo[2,3-a]quinolizine and reducing this; and (5) 2 - hydroxy - 9:10 - dimethoxy - 1:2:3:4: 6:7:12:12b - octahydro - indolo[2,3 - a] quinolizine by heating 5:6-dimethoxy-tryptamine-2-carboxylic acid with hydrochloric acid to effect decarboxylation, condensing the product with ethoxy-carbonyl pyruvic acid and subsequently esterifying as under (4) to give ethyl - 2:3:4:9 - tetrahydro - 6:7 - dimethoxy-1H - pyrid[3,4 - b]indole - 1 - acetatehydrochloride, treating this as under (4) to give 2-oxo9:10 - dimethoxy - 1:2:3:4:6:7:12:12b-octahydro - indolo[2,3 - a]quinolizine and reducing this. Hydrochlorides of some of the products are described. Ketone starting materials are prepared by the method disclosed in Specification 840,267 or by analogous methods.
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB28765/57A GB841225A (en) | 1957-09-12 | 1957-09-12 | Novel quinolizine derivatives and process for the manufacture of same |
CH6312458A CH376928A (en) | 1957-09-12 | 1958-08-21 | Process for the preparation of indolo-quinolizines |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB28765/57A GB841225A (en) | 1957-09-12 | 1957-09-12 | Novel quinolizine derivatives and process for the manufacture of same |
Publications (1)
Publication Number | Publication Date |
---|---|
GB841225A true GB841225A (en) | 1960-07-13 |
Family
ID=10280790
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB28765/57A Expired GB841225A (en) | 1957-09-12 | 1957-09-12 | Novel quinolizine derivatives and process for the manufacture of same |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB841225A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2455044A1 (en) * | 1979-04-26 | 1980-11-21 | Synthelabo | PYRIDO-INDOLES AND THEIR APPLICATION IN THERAPEUTICS |
-
1957
- 1957-09-12 GB GB28765/57A patent/GB841225A/en not_active Expired
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2455044A1 (en) * | 1979-04-26 | 1980-11-21 | Synthelabo | PYRIDO-INDOLES AND THEIR APPLICATION IN THERAPEUTICS |
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