GB1426630A - Indolo-2,3-a- quinolizine derivatives - Google Patents

Indolo-2,3-a- quinolizine derivatives

Info

Publication number
GB1426630A
GB1426630A GB1712173A GB1712173A GB1426630A GB 1426630 A GB1426630 A GB 1426630A GB 1712173 A GB1712173 A GB 1712173A GB 1712173 A GB1712173 A GB 1712173A GB 1426630 A GB1426630 A GB 1426630A
Authority
GB
United Kingdom
Prior art keywords
formula
compound
quinolizine
quinolizine derivatives
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
Application number
GB1712173A
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.)
Sandoz AG
Original Assignee
Sandoz AG
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 Sandoz AG filed Critical Sandoz AG
Publication of GB1426630A publication Critical patent/GB1426630A/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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
    • C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
    • C07C45/515—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups the singly bound functional group being an acetalised, ketalised hemi-acetalised, or hemi-ketalised hydroxyl group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/02—Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen
    • C07C47/14—Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen containing halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D461/00—Heterocyclic compounds containing indolo [3,2,1-d,e] pyrido [3,2,1,j] [1,5]-naphthyridine ring systems, e.g. vincamine

Abstract

1426630 Indole[2,3-a]quinolizine derivatives SANDOZ Ltd 10 April 1973 [14 April 1972] 17121/73 Heading C2C Indole[2,3-a]quinolizine derivatives of Formula I are prepared by reacting a compound of formula with a compound of formula wherein X is bromine or iodine and, if desired, isolating an individual optical isomer or a racemate from the resulting mixture of optical isomers. The reaction may be effected in an inert organic solvent or in hexamethyl phosphonic acid triamine at a temperature of from 10‹ to 80‹ C. 1 ethyl 1,2,3,4,5,6,7,12b -octahydroindolo[2,3-a]quinolizine - 1 - carbaldehyde and its isomers are claimed per se. The compounds of Formula II may be prepared by a process which comprises (a) reacting a cis form of the compound of Formula I with an alkali metal salt of a compound of formula wherein R 1 and R 2 are independently C 1 to C 6 alkyl to obtain a compound of Formula III (b) hydrogenating the compound of Formula III to obtain a compound of Formula IV and (c) cyclizing the compound of Formula IV to obtain the compound of Formula II.
GB1712173A 1972-04-14 1973-04-10 Indolo-2,3-a- quinolizine derivatives Expired GB1426630A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH559072A CH578001A5 (en) 1972-04-14 1972-04-14

Publications (1)

Publication Number Publication Date
GB1426630A true GB1426630A (en) 1976-03-03

Family

ID=4296140

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1712173A Expired GB1426630A (en) 1972-04-14 1973-04-10 Indolo-2,3-a- quinolizine derivatives

Country Status (7)

Country Link
JP (1) JPS4918895A (en)
BE (1) BE798160A (en)
CH (1) CH578001A5 (en)
DE (1) DE2318329A1 (en)
FR (1) FR2185624B1 (en)
GB (1) GB1426630A (en)
HU (1) HU167838B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0045918A1 (en) * 1980-08-04 1982-02-17 Paolo Corvi Mora A process for the synthesis of vincamine and related indole alkaloids

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5436898B2 (en) * 1974-06-04 1979-11-12
JPS5184160U (en) * 1974-12-27 1976-07-06
AU499923B2 (en) * 1975-06-27 1979-05-03 Richter Gedeon Vegyeszeti Gyar N Indoloquinolizine derivatives & their production
CH586698A5 (en) * 1975-07-10 1977-04-15 Sandoz Ag
FR2591225B1 (en) * 1985-12-05 1988-07-01 Yves Langlois NEW PROCESS FOR THE PREPARATION OF VINCAMINE AND ITS DERIVATIVES

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3770724A (en) * 1970-03-31 1973-11-06 Roussel Uclaf Process for preparing pentacyclic alkaloids

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0045918A1 (en) * 1980-08-04 1982-02-17 Paolo Corvi Mora A process for the synthesis of vincamine and related indole alkaloids

Also Published As

Publication number Publication date
DE2318329A1 (en) 1973-10-18
BE798160A (en) 1973-10-12
FR2185624A1 (en) 1974-01-04
CH578001A5 (en) 1976-07-30
HU167838B (en) 1975-12-25
JPS4918895A (en) 1974-02-19
FR2185624B1 (en) 1977-12-30

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Legal Events

Date Code Title Description
PS Patent sealed
PCNP Patent ceased through non-payment of renewal fee