A novel entry toward 2-imino-1, 3-thiazolidines and 2-imino-1, 3-thiazolines by ring transformation of 2-(thiocyanomethyl) aziridines

M D'hooghe, A Waterinckx…

Index: D'hooghe, Matthias; Waterinckx, Alex; De Kimpe, Norbert Journal of Organic Chemistry, 2005 , vol. 70, # 1 p. 227 - 232

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Citation Number: 74

Abstract

A new, efficient, and straightforward synthesis of 3-arylmethyl-4-chloromethyl-2-imino-1, 3- thiazolidines and 2-(N-acylimino)-3-arylmethyl-4-chloromethyl-1, 3-thiazolidines has been developed by ring transformation of 1-arylmethyl-2-(thiocyanomethyl) aziridines upon treatment with a catalytic amount of titanium (IV) chloride in dichloromethane. The latter 2- (thiocyanomethyl) aziridines were prepared in high yields from 1-arylmethyl-2-( ...