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

Abstract

By the interaction of γ-thiobutyrolactone with bis(dimethylamino)-tert-butoxymethane, α-dimethylaminomethylene-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 4,9-dihydrothiopyrano[3,4-b]indol-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-thiopyrano[4′,3′:4,5]pyrrolo[3,2,1-ij]quinolin-8-ones, representatives of a new heterocyclic system.

How to Cite
Tokmakov, G. P. Chem. Heterocycl. Compd. 1996, 32, 158. [Khim. Geterotsikl. Soedin. 1996, 180.]

For this article in the English edition, see DOI https://doi.org/10.1007/BF01165438