A Convenient Synthesis of 2-Aryl- and 2-Arylamino-4-aryl-5-cyanothiazoles

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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-1. N-Monosubstituted enaminonitriles 1g,h react with 2a affording 3-substituted 2-phenylimino-.DELTA.4-thiazolines 6a,b, but in very poor yields. A mechanism which accounts for the formation of thiazole and thiazoline structures is presented.
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