Reactions of thionyl chloride with C-methyl heterocycles. Part 1. The formation of dichloro(2-quinolyl)methanesulphenyl chlorides from 2-methylquinolines

Abstract

Hot thionyl chloride converts 2-methylquinolines (1) into dichloro(2-quinolyl)methanesulphenyl chlorides (2) which upon treatment with secondary amines are transformed into thioamides (7). Reaction of the novel derivatives (2) with amidines gives 5-(2-quinolyl)-1,2,4-thiadiazoles (8) and reaction with anionic nucleophiles results in substitution at sulphur.