Six-membered cyclic semiaminal as intermediate in the synthesis of thiazoles from thiosemicarhazide and α-haloketones

Abstract

Cyclization of thiosemicarbazide with methyl 3-chloro-2-oxo-3-phenylpropionate in MeCN results in 5-hydroxy-2-imino-5-methoxycarbonyl-6-phenylperhydro-1,3,4-thiadiazine. The structure of the product has been confirmed using spectral (IR,1H,13C,13C{1H} NMR) methods and chemical transformations. © 1994 Plenum Publishing Corporation