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

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Chemistry of Heterocyclic Compounds Aims and scope

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.

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Authors and Affiliations

  1. K. A. Timiryazev Moscow Agricultural Academy, 127550, Moscow

    G. P. Tokmakov

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  1. G. P. Tokmakov
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 180–185, February, 1996.

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Tokmakov, G.P. α-Dimethylaminomethylene-γ-thiobutyrolactone and synthesis of heterocyclic derivatives. Chem Heterocycl Compd 32, 158–162 (1996). https://doi.org/10.1007/BF01165438

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  • DOI: https://doi.org/10.1007/BF01165438

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