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The reaction of (N-isocyanimino) triphenylphosphorane with (E)-3-aryl-2- propenoic acid derivatives: One-pot synthesis of 2-[(E)-2-aryl-1-ethenyl]-1,3,4-oxadiazoles via intramolecular aza-Wittig reaction

โœ Scribed by Hamideh Ahankar; Ali Ramazani; Issa Amini; Yavar Ahmadi; Ali Souldozi


Publisher
John Wiley and Sons
Year
2011
Tongue
English
Weight
82 KB
Volume
22
Category
Article
ISSN
1042-7163

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โœฆ Synopsis


Abstract

The reaction of (E)โ€3โ€arylโ€2โ€propenoic acid derivatives with (Nโ€isocyanimino) triphenylphosphorane proceeds smoothly at room temperature to afford the corresponding 2โ€[(E)โ€2โ€arylโ€1โ€ethenyl]โ€1,3,4โ€oxadiazole via an intramolecular azaโ€Wittig reaction in good yields under neutral conditions. The structures of the products were deduced from their IR, ^1^H NMR, and ^13^C NMR spectra and mass spectrometry. ยฉ 2011 Wiley Periodicals, Inc. Heteroatom Chem 22:612โ€“616, 2011; View this article online at wileyonlinelibrary.com. DOI 10.1002/hc.20701


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## Abstract The iminium intermediate formed by the reaction of a secondary amine with acetaldehyde was reacted by (__N__โ€isocyanimino) triphenylphosphorane in the presence of an electronโ€poor (__E__)โ€cinnamic acid derivative to give the corresponding iminophosphorane intermediate, whose intramolecu