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Efficient one-pot synthesis of disubstituted 1,3,4-oxadiazole derivatives from the reaction of (N-isocyanimino)triphenylphosphorane, acetaldehyde, a secondary amine, and an electron-poor (E)-cinnamic acid

✍ Scribed by Ali Ramazani; Yavar Ahmadi; Roghayeh Tarasi

Publisher
John Wiley and Sons
Year
2010
Tongue
English
Weight
165 KB
Volume
22
Category
Article
ISSN
1042-7163

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✦ Synopsis

Abstract

The iminium intermediate formed by the reaction of a secondary amine with acetaldehyde was reacted by (N‐isocyanimino) triphenylphosphorane in the presence of an electron‐poor (E)‐cinnamic acid derivative to give the corresponding iminophosphorane intermediate, whose intramolecular the aza‐Wittig reaction led to disubstituted 1,3,4‐oxadiazole derivatives. The reactions were completed under neutral conditions at room temperature, and the corresponding disubstituted 1,3,4‐oxadiazole derivatives were produced in excellent yields. © 2010 Wiley Periodicals, Inc. Heteroatom Chem 22:79–84, 2011; View this article online at wileyonlinelibrary.com. DOI 10.1002/hc.20660

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