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Chemistry of Heterocyclic Compounds

, Volume 32, Issue 2, pp 158–162 | Cite as

α-Dimethylaminomethylene-γ-thiobutyrolactone and synthesis of heterocyclic derivatives

  • G. P. Tokmakov
Article

Abstract

By the interaction of γ-thiobutyrolactone with bis(dimethylamino)-tert-butoxymethane, α-dimethylamino-methylene-γ-thiobutyrolactone has been obtained. Its reactions with arylhydrazines have been investigated. With phenylhydrazine, 4-(2-mercaptoethyl)-1 phenylpyrazolone-5 is formed; but with α-substituted phenylhydrazines, as a result of the Fischer reaction and expansion of the thiolactone ring, 9-substituted 4, 9dihydrothiopyrano[3,4-bjindol-1(3H)-ones are formed. Analogous reactions with 1-amino derivatives of tetrahydroquinoline and tetrahydroquinaldine lead to the formation of 5, 6,10,11-tetrahydro-4H, 8H-thiopyruno(4′,3′:4,5jpyrrolo[3,2,1-ijlquinolin-8-ones, representatives of a new heterocyclic system.

Keywords

Organic Chemistry Dimethylamino Analogous Reaction Phenylhydrazine Heterocyclic System 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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Copyright information

© Plenum Publishing Corporation 1996

Authors and Affiliations

  • G. P. Tokmakov
    • 1
  1. 1.K. A. Timiryazev Moscow Agricultural AcademyMoscow

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