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GB958936A - Process for the production of quinolizine derivatives - Google Patents

Process for the production of quinolizine derivatives

Info

Publication number
GB958936A
GB958936A GB1023762A GB1023762A GB958936A GB 958936 A GB958936 A GB 958936A GB 1023762 A GB1023762 A GB 1023762A GB 1023762 A GB1023762 A GB 1023762A GB 958936 A GB958936 A GB 958936A
Authority
GB
United Kingdom
Prior art keywords
hydrogen atom
alkyl
quaternary
stand
straight
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
GB1023762A
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.)
MTA
Magyar Tudomanyos Akademia
Original Assignee
MTA
Magyar Tudomanyos Akademia
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 MTA, Magyar Tudomanyos Akademia filed Critical MTA
Publication of GB958936A publication Critical patent/GB958936A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
    • C07D491/14—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
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
    • C07C49/203—Unsaturated compounds containing keto groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
    • C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
    • C07D217/10—Quaternary compounds
    • 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

Landscapes

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

Abstract

Quinolizine derivatives of the general formula: <FORM:0958936/C2/1> wherein R1-R4 each stand for a hydrogen atom or for an alkyl or alkoxy group with a straight or branched carbon chain containing from 1-10 carbon atoms, R5-R8 each stand for a hydrogen atom, an alkyl group with a straight or branched carbon chain containing from 1-10 carbon atoms or an aryl or aralkyl group, at least one of R5, R6 and R7 being other than a hydrogen atom, are obtained in a process which comprises subjecting a quaternary 3, 4-dihydro-isoquinolinium salt of the general formula: <FORM:0958936/C2/2> (wherein R1-R8 are as defined above and X stands for the anion of a strong acid) to cyclisation in the presence of a basic agent. The quaternary dihydro isoquinolinium salts can be obtained by reacting the corresponding 3, 4-dihydroisoquinoline derivatives with an alkyl vinyl ketone e.g. methyl vinyl ketone, and may be treated directly with bases without isolation from the reaction mixture.
GB1023762A 1961-03-28 1962-03-16 Process for the production of quinolizine derivatives Expired GB958936A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
HUMA001026 1961-03-28

Publications (1)

Publication Number Publication Date
GB958936A true GB958936A (en) 1964-05-27

Family

ID=10998369

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1023762A Expired GB958936A (en) 1961-03-28 1962-03-16 Process for the production of quinolizine derivatives

Country Status (4)

Country Link
AT (1) AT238201B (en)
CH (1) CH429734A (en)
DE (1) DE1253271B (en)
GB (1) GB958936A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR101409335B1 (en) * 2011-08-17 2014-06-23 충북대학교 산학협력단 Methods for Stereoselective Synthesis of Tetrabenazine
US20220267317A1 (en) * 2008-09-18 2022-08-25 Auspex Pharmaceuticals, Inc. Benzoquinoline Inhibitors of Vesicular Monoamine Transporter 2

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1134678B (en) * 1959-09-24 1962-08-16 Hoffmann La Roche Process for the preparation of 2-oxo-benzoquinolizines and their salts

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20220267317A1 (en) * 2008-09-18 2022-08-25 Auspex Pharmaceuticals, Inc. Benzoquinoline Inhibitors of Vesicular Monoamine Transporter 2
KR101409335B1 (en) * 2011-08-17 2014-06-23 충북대학교 산학협력단 Methods for Stereoselective Synthesis of Tetrabenazine

Also Published As

Publication number Publication date
DE1253271B (en) 1967-11-02
CH429734A (en) 1967-02-15
AT238201B (en) 1965-01-25

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