GB1024902A - A process for the preparation of optically active benzo[a]quinolizine derivatives - Google Patents

A process for the preparation of optically active benzo[a]quinolizine derivatives

Info

Publication number
GB1024902A
GB1024902A GB11454/65A GB1145465A GB1024902A GB 1024902 A GB1024902 A GB 1024902A GB 11454/65 A GB11454/65 A GB 11454/65A GB 1145465 A GB1145465 A GB 1145465A GB 1024902 A GB1024902 A GB 1024902A
Authority
GB
United Kingdom
Prior art keywords
alkyl
benzo
optically active
tetrahydro
alkoxycarbonylmethyl
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
GB11454/65A
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.)
F Hoffmann La Roche AG
Original Assignee
F Hoffmann La Roche 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 F Hoffmann La Roche AG filed Critical F Hoffmann La Roche AG
Publication of GB1024902A publication Critical patent/GB1024902A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D455/00—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
    • C07D455/03—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
    • C07D455/04—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing a quinolizine ring system condensed with only one six-membered carbocyclic ring, e.g. julolidine
    • C07D455/06—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing a quinolizine ring system condensed with only one six-membered carbocyclic ring, e.g. julolidine containing benzo [a] quinolizine ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D455/00—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
    • C07D455/03—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
    • C07D455/04—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing a quinolizine ring system condensed with only one six-membered carbocyclic ring, e.g. julolidine
    • C07D455/06—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing a quinolizine ring system condensed with only one six-membered carbocyclic ring, e.g. julolidine containing benzo [a] quinolizine ring systems
    • C07D455/08—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing a quinolizine ring system condensed with only one six-membered carbocyclic ring, e.g. julolidine containing benzo [a] quinolizine ring systems having an isoquinolyl-1, a substituted isoquinolyl-1 or an alkylenedioxyisoquinolyl-1 radical linked through only one carbon atom, attached in position 2, e.g. emetine

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention comprises optically active 2-(alkoxycarbonylmethyl) - 3 - alkyl - 9,10 - di - methoxy - 1,4,6,7 - tetrahydro - 11bH - benzo [a]quinolizines where the alkyl and alkoxy radicals contain not more than 4 carbon atoms, and compounds of the formulae <FORM:1024902/C2/1> (wherein R and R1 represent C1-4 alkyl radicals) and acid addition salts of the compounds of the Formula III having the tautomeric formula <FORM:1024902/C2/2> (wherein X1 represents an anion). (+)-2-(Alkoxycarbonylmethyl - 3 - alkyl - 9,10 - dimethoxy - 1,4,6,7 - tetrahydro - 11bH - benzo [a]quinolizine may be obtained by separating a racemic-mixture of the (+) and (-) forms by, for example, fractional crystallization of the optically active salts with an optically active acid. (-)-2-(Alkoxycarbonylmethyl) - 3 - alkyl-9, 10 - dimethoxy - 1,4,6,7 - tetrahydro - 11bH-benzo[a]quinolizine is made by oxidizing the corresponding (+) isomer with a mercuric, cupric or ferric salt to give a compound of the Formula III and reducing said oxidation product and separating the resulting racemic 2-(lower alkoxycarbonylmethyl) - 3 - (lower alkyl) - 9,10 - dimethoxy - 1,4,6,7 - tetrahydro-11bH - benzo[a]quinolizine into its (+) and (-) forms and, if desired, recycling the (+)-form.
GB11454/65A 1962-03-21 1963-03-21 A process for the preparation of optically active benzo[a]quinolizine derivatives Expired GB1024902A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH338662A CH419138A (en) 1962-03-21 1962-03-21 Process for the preparation of enantiomeric compounds from the dehydroemetin series

Publications (1)

Publication Number Publication Date
GB1024902A true GB1024902A (en) 1966-04-06

Family

ID=4254829

Family Applications (4)

Application Number Title Priority Date Filing Date
GB11168/63A Expired GB1024901A (en) 1962-03-21 1963-03-21 A process for the manufacture of dehydro-emetines and analogues thereof
GB11454/65A Expired GB1024902A (en) 1962-03-21 1963-03-21 A process for the preparation of optically active benzo[a]quinolizine derivatives
GB43797/65A Expired GB1024903A (en) 1962-03-21 1963-03-21 Novel homoveratryl amides
GB43798/65A Expired GB1024904A (en) 1962-03-21 1963-03-21 Novel psychotrine derivatives

Family Applications Before (1)

Application Number Title Priority Date Filing Date
GB11168/63A Expired GB1024901A (en) 1962-03-21 1963-03-21 A process for the manufacture of dehydro-emetines and analogues thereof

Family Applications After (2)

Application Number Title Priority Date Filing Date
GB43797/65A Expired GB1024903A (en) 1962-03-21 1963-03-21 Novel homoveratryl amides
GB43798/65A Expired GB1024904A (en) 1962-03-21 1963-03-21 Novel psychotrine derivatives

Country Status (10)

Country Link
BE (1) BE629898A (en)
BR (1) BR6347679D0 (en)
CH (1) CH419138A (en)
CY (1) CY376A (en)
DE (1) DE1445875A1 (en)
DK (2) DK123654B (en)
ES (1) ES286240A1 (en)
GB (4) GB1024901A (en)
MY (1) MY6700083A (en)
OA (1) OA00962A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4686226A (en) * 1985-09-03 1987-08-11 Merck & Co., Inc. Substituted benzo[b]furo- and benzo[b]thieno quinolizines

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4686226A (en) * 1985-09-03 1987-08-11 Merck & Co., Inc. Substituted benzo[b]furo- and benzo[b]thieno quinolizines

Also Published As

Publication number Publication date
GB1024901A (en) 1966-04-06
DK123654B (en) 1972-07-17
BR6347679D0 (en) 1973-08-02
DE1445875A1 (en) 1969-04-10
OA00962A (en) 1968-08-07
DE1545946B2 (en) 1975-06-19
DK107613C (en) 1967-06-19
CY376A (en) 1967-03-01
MY6700083A (en) 1967-12-31
GB1024903A (en) 1966-04-06
GB1024904A (en) 1966-04-06
BE629898A (en) 1963-10-21
ES286240A1 (en) 1963-11-16
CH419138A (en) 1966-08-31
DE1545946A1 (en) 1970-04-09

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