GB840267A - Manufacture of quinolizine derivatives - Google Patents

Manufacture of quinolizine derivatives

Info

Publication number
GB840267A
GB840267A GB3349457A GB3349457A GB840267A GB 840267 A GB840267 A GB 840267A GB 3349457 A GB3349457 A GB 3349457A GB 3349457 A GB3349457 A GB 3349457A GB 840267 A GB840267 A GB 840267A
Authority
GB
United Kingdom
Prior art keywords
ester
alkyl
pyrid
indole
carboxymethyl
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
Application number
GB3349457A
Inventor
Peter George Philpott
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Roche Products Ltd
Original Assignee
Roche Products Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Roche Products Ltd filed Critical Roche Products Ltd
Priority to GB3349457A priority Critical patent/GB840267A/en
Publication of GB840267A publication Critical patent/GB840267A/en
Expired legal-status Critical Current

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
    • C07D471/12—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 three hetero rings
    • C07D471/14—Ortho-condensed systems

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

The invention comprises compounds of the general formula <FORM:0840267/IV(b)/1> (wherein R is an alkyl group) and salts thereof; and their preparation by condensing an ester of 1 - carboxymethyl - 2 : 3 : 4 : 9 - tetrahydro1H-pyrid [3 : 4-b] indole with an alpha-alkylacrylic acid ester, cyclizing the resulting diester of 1 - carboxymethyl - 2 - (21 - alkyl - 21-carboxy - ethyl) - 2 : 3 : 4 : 9 - tetrahydro - 1H-pyrid [3 : 4-b] indole in a Dieckmann cyclization and hydrolysing and decarboxylating the resulting ester of 1 - carboxy - 2 - oxo - 3 - alkyl-1 : 2 : 3 : 4 : 6 : 7 : 12 : 12b - octahydro - indolo [2 : 3-a]quinolizine. Either or both of the ester starting materials are advantageously ethyl or methyl esters, the cyclization may conveniently be carried out by heating the crude product of the condensation step in an inert solvent with an alkali metal alkoxide, and the hydrolysis and decarboxylation are conveniently effected by refluxing the cyclized product with hydrochloric acid. Preferably all the process steps are carried out in an inert atmosphere. An example is given.
GB3349457A 1957-10-28 1957-10-28 Manufacture of quinolizine derivatives Expired GB840267A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB3349457A GB840267A (en) 1957-10-28 1957-10-28 Manufacture of quinolizine derivatives

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB3349457A GB840267A (en) 1957-10-28 1957-10-28 Manufacture of quinolizine derivatives

Publications (1)

Publication Number Publication Date
GB840267A true GB840267A (en) 1960-07-06

Family

ID=10353703

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3349457A Expired GB840267A (en) 1957-10-28 1957-10-28 Manufacture of quinolizine derivatives

Country Status (1)

Country Link
GB (1) GB840267A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3542799A (en) * 1968-08-14 1970-11-24 Warner Lambert Pharmaceutical 4,4a,6,7,12,12b,13,13a-octahydro-1h-pyrido(1,2-a:3,4-b')diindol-3(2h)-ones

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3542799A (en) * 1968-08-14 1970-11-24 Warner Lambert Pharmaceutical 4,4a,6,7,12,12b,13,13a-octahydro-1h-pyrido(1,2-a:3,4-b')diindol-3(2h)-ones

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