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BY-NC-ND 3.0 license Open Access Published by De Gruyter June 2, 2014

Four-component Synthesis of 1,3,4-Oxadiazole Derivatives from (N-Isocyanimino)triphenylphosphorane, (E)-Cinnamic Acids, Acetaldehyde and Secondary Amines

Ali Ramazani EMAIL logo , Yavar Ahmadi and Fatemeh Zeinali Nasrabadi

The 1 : 1 iminium intermediate, generated by the addition of a secondary amine to acetaldehyde is trapped by the (N-isocyanimino)triphenylphosphorane in the presence of an (E)-cinnamic acid derivative, leading to the formation of the corresponding iminophosphorane intermediate. Disubstituted 1,3,4-oxadiazole derivatives are formed via intramolecular aza-Wittig reaction of the iminophosphorane intermediates. The reactions were completed under neutral conditions at room temperature, and the corresponding disubstituted 1,3,4-oxadiazole derivatives were produced in excellent yields.

Graphical Abstract

 Four-component Synthesis of 1,3,4-Oxadiazole Derivatives from (N-Isocyanimino)triphenylphosphorane, (E)-Cinnamic Acids, Acetaldehyde and Secondary Amines

Four-component Synthesis of 1,3,4-Oxadiazole Derivatives from (N-Isocyanimino)triphenylphosphorane, (E)-Cinnamic Acids, Acetaldehyde and Secondary Amines

Received: 2010-10-13
Published Online: 2014-6-2
Published in Print: 2011-2-1

© 1946 – 2014: Verlag der Zeitschrift für Naturforschung

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.

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