Effect of Substituents on the Regioselectivity of the Reaction of α??Tosyloxyketones with Thioureas in Acidic Medium: Access to 2??Aminothiazoles and 2??Imino??2, 3?? …

…, R Kumar, D Sanz, RM Claramunt

Index: Aggarwal, Ranjana; Kumar, Rajiv; Sanz, Dionisia; Claramunt, Rosa M. Journal of Heterocyclic Chemistry, 2014 , vol. 51, # 3 p. 598 - 603

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Abstract

Abstract Regioselective condensation of α-tosyloxyacetophenones 1 and N-substituted thioureas 2 in acidic medium to give regioisomers 2-aminothiazoles I and 2-imino-2, 3- dihydrothiazoles II is largely influenced by the substituents present on 1 and 2. A mechanism, supported by DFT calculations has been proposed to explain the observed regioselectively.