GB1459210A - Method for the synthesis of plus-minus-glaziovine - Google Patents

Method for the synthesis of plus-minus-glaziovine

Info

Publication number
GB1459210A
GB1459210A GB5866273A GB5866273A GB1459210A GB 1459210 A GB1459210 A GB 1459210A GB 5866273 A GB5866273 A GB 5866273A GB 5866273 A GB5866273 A GB 5866273A GB 1459210 A GB1459210 A GB 1459210A
Authority
GB
United Kingdom
Prior art keywords
formula
glaziovine
ylide
group
dihydroglaziovine
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
GB5866273A
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.)
Siphar SA
Original Assignee
Siphar SA
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 Siphar SA filed Critical Siphar SA
Publication of GB1459210A publication Critical patent/GB1459210A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
    • C07D221/20—Spiro-condensed ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
    • C07D221/04—Ortho- or peri-condensed ring systems
    • C07D221/06—Ring systems of three rings
    • C07D221/16—Ring systems of three rings containing carbocyclic rings other than six-membered

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Other In-Based Heterocyclic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

1459210 Glaziovine SIPHAR SA 18 Dec 1973 [22 Dec 1972] 58662/73 Heading C2C (Œ)-Glaziovine of Formula (I) is prepared according to the following reaction scheme wherein R is a hydrogen atom or an alkyl group having from one to four carbon atoms, R 1 is an alkyl group having from one to four carbon atoms, R 2 is a hydrogen atom or an aliphatic or aromatic acyl group, e.g. the acetyl or benzoyl group, characterized by comprising the steps of subjecting the 6,7-dimethoxy-2-methyl- 1,2,3,4 - tetrahydroisoquinolinyl - 1 - acetic acid of Formula (13) or an ester thereof to cyclization and selective demethylation of the 7-methoxy group by heating in polyphosphoric acid to obtain the tricyclo hydroxyketone of formula (12), bringing the compound (12) to react with a phosphorus ylide of Formula (14) according to the Wittig reaction in a solution in dimethylsulphoxide at 20-25‹ C. and for 5-12 hours, by addition of a solution of ylide (14) as obtained from triphenylmethoxymethylphosphonium chloride and sodium methylsulphinylmethide in an amount of 2À5-5 mol of ylide per mol of hydroxyketone to obtain an enol-ether of Formula (15), converting the enol-ether, by acidic hydrolysis, into the aldehyde of Formula (16), condensing the aldehydc (16) with methyl vinyl ketone in the presence of a basic catalyst selected from alkali metal hydroxides and alcoholates; quaternary ammonium hydroxides; and strong organic tertiary bases according to the Robinson ring-formation reaction to obtain the novel (Œ)-dihydroglaziovine of Formula (17), (R 2 =H); brominating an O-acyl-derative of (Œ)-dihydroglaziovine of Formula (17) (R 2 = aliphatic or aromatic acyl) with bromine or N-bromosuccinimide in the presence of 5-10 mols of a strong mineral acid per mole of compound to be brominated in an inert solvent to give the corresponding bromo derivative of Formula (18) and subjecting the latter to dehydrohalogenation and saponification to obtain (Œ)-glaziovine of Formula (1). (Œ)Glaziovine has tranquillizing and antianxiety activity.
GB5866273A 1972-12-22 1973-12-18 Method for the synthesis of plus-minus-glaziovine Expired GB1459210A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH1878372A CH588467A5 (en) 1972-12-22 1972-12-22

Publications (1)

Publication Number Publication Date
GB1459210A true GB1459210A (en) 1976-12-22

Family

ID=4435260

Family Applications (1)

Application Number Title Priority Date Filing Date
GB5866273A Expired GB1459210A (en) 1972-12-22 1973-12-18 Method for the synthesis of plus-minus-glaziovine

Country Status (5)

Country Link
JP (1) JPS539224B2 (en)
CH (1) CH588467A5 (en)
DE (1) DE2363531A1 (en)
FR (1) FR2211459A1 (en)
GB (1) GB1459210A (en)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5885395U (en) * 1981-12-02 1983-06-09 三菱電線工業株式会社 Blocked “hei” body
JPS593999A (en) * 1982-06-29 1984-01-10 日本電気株式会社 Shield cover for cable
US4639545A (en) * 1984-02-07 1987-01-27 Raychem Limited Recoverable article for screening
JPS63115297U (en) * 1987-01-21 1988-07-25
JPH0720955Y2 (en) * 1987-05-28 1995-05-15 横河・ヒユーレツト・パツカード株式会社 Flexible shield tube
JPH0215798U (en) * 1988-07-15 1990-01-31
JPH0320495U (en) * 1989-07-10 1991-02-28
JPH0443821U (en) * 1990-08-17 1992-04-14

Also Published As

Publication number Publication date
FR2211459A1 (en) 1974-07-19
JPS504080A (en) 1975-01-16
JPS539224B2 (en) 1978-04-04
CH588467A5 (en) 1977-06-15
DE2363531A1 (en) 1974-06-27

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Legal Events

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