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
โ 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
- DOI
- 10.1002/hc.20701
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โฆ Synopsis
Abstract
The reaction of (E)โ3โarylโ2โpropenoic acid derivatives with (Nโisocyanimino) triphenylphosphorane proceeds smoothly at room temperature to afford the corresponding 2โ[(E)โ2โarylโ1โethenyl]โ1,3,4โoxadiazole via an intramolecular azaโWittig 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 22:612โ616, 2011; View this article online at wileyonlinelibrary.com. DOI 10.1002/hc.20701
๐ SIMILAR VOLUMES
Reactions of biacetyl (ยผ butane-2,3-dione) with (N-isocyanimino)triphenylphosphorane in the presence of aromatic carboxylic acids proceed smoothly at room temperature and under neutral conditions to afford 3-(5-aryl-1,3,4-oxadiazol-2-yl)-3-hydroxybutan-2-one derivatives in high yields. Introduction
## Abstract The iminium intermediate formed by the reaction of a secondary amine with acetaldehyde was reacted by (__N__โisocyanimino) triphenylphosphorane in the presence of an electronโpoor (__E__)โcinnamic acid derivative to give the corresponding iminophosphorane intermediate, whose intramolecu