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

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

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 re...

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Veröffentlicht in:Heteroatom chemistry 2011, Vol.22 (1), p.79-84
Hauptverfasser: Ramazani, Ali, Ahmadi, Yavar, Tarasi, Roghayeh
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Ahmadi, Yavar
Tarasi, Roghayeh
description 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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title 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
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