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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 40, 2010 - Issue 16
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Original Articles

Simple and Highly Efficient Procedure for Conversion of Aldoximes to Nitriles Using N-(p-Toluenesulfonyl) Imidazole

, , , &
Pages 2429-2440 | Received 18 Jul 2009, Published online: 26 Jul 2010
 

Abstract

A facile and efficient method for dehydration of aldoximes into nitriles using N-(p-toluenesulfonyl) imidazole (TsIm) is described. In this method, aldoximes were refluxed with TsIm in the presence of 1,8-diazabicyclo-[5.4.0]undec-7-ene (DBU) in dimethylformamide (DMF) to afford the corresponding nitriles in good yields. This methodology is highly efficient for various structurally diverse aldoximes including aromatic, heteroaromatic, and aliphatic oximes. A plausible mechanism for the conversion of aldoxime into nitriles using TsIm/DBU is explained.

ACKNOWLEDGMENT

We thank the Shiraz University of Technology and Shiraz University Research Councils for partial support of this work.

Notes

a Anhydrous DMF.

b Isolated yield.

c No reaction.

d 1:1 ratio.

a Isolated yield.

a Isolated yield.

b No reaction.

a Isolated yield.

a All products were characterized by 1H and 13C NMR, IR, CHN, and MS analysis.

b IR signal of nitrile in wavenumbers (cm−1).

c Isolated yield.

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