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

1988; Issue: 11 Linguagem: Inglês

10.1039/p19880003019

2050-8255

A. H. M. AL‐SHAAR, David W. Gilmour, David J. Lythgoe, I. McClenaghan, Christopher A. Ramsden,

Structural and Chemical Analysis of Organic and Inorganic Compounds

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.