One-pot, four-component synthesis of fully substituted 1,3,4-oxadiazole derivatives from N-isocyaniminotriphenylphosphorane (Ph3PNNC), a primary amine, a carboxylic acid and cinnamaldehyde

Kalantari, Fatemeh; Ramazani, Ali; Zeinali Nasrabadi, Fatemeh

Document Type : Original Research Article

Authors

¹ Department of Chemistry, University of Zanjan, P O Box 45195-313, Zanjan, Iran

² Department of Chemistry, Payame Noor University, P.O. Box 19395-3697, Tehran, Iran

Abstract

The imine intermediate generated by the addition of primary amine to the cinnamaldehyde is trapped by the N-isocyaniminotriphenylphosphorane (Ph3PNNC) and a carboxylic acid, and leads to the formation of the corresponding iminophosphorane intermediate. The 1,3,4-oxadiazole derivatives are formed via intramolecular aza-Wittig reaction of the iminophosphorane intermediate. The reactions were completed under neutral conditions at room temperature. The fully substituted 1,3,4-oxadiazole derivatives were produced in high yields. The method offers a mild, simple, and efficient route for the preparation of fully substituted 1,3,4-oxadiazols. The structures of the products were deduced from their IR, 1H NMR, 13C NMR spectra, and mass spectrometry.

Graphical Abstract

Keywords

Main Subjects

Organic chemistry

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Iranian chemical communication

One-pot, four-component synthesis of fully substituted 1,3,4-oxadiazole derivatives from N-isocyaniminotriphenylphosphorane (Ph3PNNC), a primary amine, a carboxylic acid and cinnamaldehyde

References

References

Volume 4, Issue 2, pp. 133-235, Serial No. 11
April 2016
Pages 155-164

One-pot, four-component synthesis of fully substituted 1,3,4-oxadiazole derivatives from N-isocyaniminotriphenylphosphorane (Ph3PNNC), a primary amine, a carboxylic acid and cinnamaldehyde

References

References

Volume 4, Issue 2, pp. 133-235, Serial No. 11April 2016Pages 155-164

Volume 4, Issue 2, pp. 133-235, Serial No. 11
April 2016
Pages 155-164