Efficient synthesis of new oxadiazole-thiazole hybrids using (diacetoxyiodo)benzene

Abstract

An efficient synthesis of some new 2-aryl-5-(2'-(4-nitrophenylamino)thiazol-4'-yl)-1,3,4-oxadiazoles <strong>7a-e</strong>, has been accomplished through oxidative cyclization of 2-(4-nitrophenylamino)-<em>N'</em>-(substituted benzylidene) thiazole-4-carbohydrazides <strong>6a-e</strong> using an ecofriendly oxidant, (diacetoxyiodo)benzene at ambient temperature. The structures of the synthesized oxadiazole-thiazole hybrid compounds have been characterized by elemental and spectral (IR, ¹H and ¹³C NMR, and MS) analysis. The reaction can tolerate a wide range of aldehydes to afford the corresponding unsymmetrical 2,5-disubstituted 1,3,4-oxadiazoles. The mild reaction conditions, relatively benign nonmetallic oxidant and short reaction time are noteworthy advantages of this methodology.