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

Condensation of carboxylic acids with benzohydrazide in the presence of TBTU afforded diacylhydrazine intermediates that underwent a smooth TsCl-mediated cyclodehydration reaction to afford 2-phenyl-5-substituted-1,3,4-oxadiazoles in good to very good yields. A mild, general, convenient, and efficie...

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Bibliographic Details
Published in:Tetrahedron letters 2010-09, Vol.51 (37), p.4801-4805
Main Authors: Stabile, Paolo, Lamonica, Alessandro, Ribecai, Arianna, Castoldi, Damiano, Guercio, Giuseppe, Curcuruto, Ornella
Format: Article
Language:English
Subjects:
1,3,4-Oxadiazoles
Cyclodehydration
One-pot synthesis
Tosyl chloride
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Summary:Condensation of carboxylic acids with benzohydrazide in the presence of TBTU afforded diacylhydrazine intermediates that underwent a smooth TsCl-mediated cyclodehydration reaction to afford 2-phenyl-5-substituted-1,3,4-oxadiazoles in good to very good yields. 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.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2010.06.139