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Report | Regular issue | Vol 23, No. 10, 1985, pp.2645-2649
Published online, 1st January, 1970
DOI: 10.3987/R-1985-10-2645
A Convenient Synthesis of 2-Aryl- and 2-Arylamino-4-aryl-5-cyanothiazoles

Antonino Corsaro* and Giovanni Puglisi

*Dipartimento di Scienze Chimiche, Università di Catania, Viale A. Doria 8, I-95125 Catania, Italy

Abstract

The reactions of a series of para-substituted 3-amino-3-aryl-propenenitriles 1a-f with N-phenyl- (2a) and N-methyl-S-chloroisothiocarbamoyl chloride (2b), followed by triethylamine treatment, provide 2-phenyl- and 2-methyl-4-aryl-5-cyanothiazoles 3a-i. N-Monosubstituted enaminonitriles 1g,h react with 2a affording 3-substituted 2-phenylimino-δ4-thiazolines 6a,b, but in very poor yields. A mechanism which accounts for the formation of thiazole and thiazoline structures is presented.