Mild and convenient one-pot synthesis of 1, 3, 4-oxadiazoles

P Stabile, A Lamonica, A Ribecai, D Castoldi…

Index: Stabile, Paolo; Lamonica, Alessandro; Ribecai, Arianna; Castoldi, Damiano; Guercio, Giuseppe; Curcuruto, Ornella Tetrahedron Letters, 2010 , vol. 51, # 37 p. 4801 - 4805

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Citation Number: 30

Abstract

A mild, general, convenient, and efficient one-pot synthesis of 2-phenyl-5-substituted-1, 3, 4- oxadiazoles is described. Both (hetero) aryl and alkyl carboxylic acids were efficiently condensed with benzohydrazide in the presence of TBTU to give diacylhydrazine intermediates. The latter underwent a smooth TsCl-mediated cyclodehydration reaction to afford 2-phenyl-5-substituted-1, 3, 4-oxadiazoles in good to very good yields.