A practical access to novel 2-amino-5-arylidene-1,3-thiazol-4(5H)-ones via sulfur/nitrogen displacement under solvent-free microwave irradiation

Abstract

A new effective approach to the synthesis of a small library of 2-amino-5-arylidene-1,3-thiazol-4(5H)-ones was reported using solvent-free reaction conditions under microwave irradiation. In the first step, rhodanines were subjected to Knoevenagel condensation with aryl aldimines according to a facile one-pot protocol. Then the (5Z)-5-arylidene rhodanine derivatives were transformed directly into the corresponding 2-amino-1,3-thiazol-4(5H)-ones by sulfur/nitrogen displacement reaction under microwaves with retention of configuration and good overall yields. © 2007 Elsevier Ltd. All rights reserved.