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■ 2,6-Dimethyl-3-cyano-4-thioxothiopyran and Related Molecules from Enaminonitriles and Hydrogen Sulfide by Phase Transfer Catalysis

Jean-Pierre Roggero,* Serge Coen, Bernard Ragonnet, and Catherine Viellescazes

*Faculté des Sciences, Laboratorie de Chimie Organique, 33, rue Louis Pasteur, 84000 Avignon, France

Abstract

3-Aminocrotonitrile reacts with H₂S in the presence of a phase transfer catalyst to yield 2,6-dimethyl-3-cyano-4-thioxothiopyran (liquid-solid catalysis) or the 4-oxo homolog (liquid-liquid catalysis). In the absence of hydrogen sulfide, 2,6-dimethyl-3-cyano-4-pyrone is obtained. The reaction mechanism is discussed.