SnCl4-mediated one-pot synthesis of 2,4,5-trisubstituted thiazoles from nitro-substituted donor–acceptor cyclopropanes and thioamides

Abstract

The treatment of nitro-substituted donor–acceptor cyclopropanes (DACs) with SnCl₄ and the subsequent reaction with thioamides provide one-pot access to various thiazole derivatives. Aroylmethylidene malonates were produced as intermediates in the reactions and they underwent conjugate addition followed by cyclocondensation with thioamides to afford the products. This work demonstrates the versatility of this class of cyclopropanes in synthesizing all three 1,3-azoles.