Reactions of thioureas and thioamides with aroylphenylacetylenes

Abstract

p-Methoxybenzoyl-, p-chlorobenzoyl- and benzoyl-phenylacetylenes (1a-c) reacted with a variety of thiocarbonyl compounds (2a-f) in methanol to give mixtures of (Z,Z)-3,3'-thiodi(1-aryl-3-phenyl- prop-2-en-1-ones) (3) and their (E,Z)-isomers (4). Configurational assignments of the products were based on N.M.R. as well as i.r. and u.v. spectra. Conversion of (4) into the corresponding (3) was also undertaken. Refluxing (3) and (4) with hydrazine or phenylhydrazine gave the corresponding pyrazoles (5) or (6).