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

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.

Keywords:

• Aldoximes
• DBU
• dehydration
• DMF
• nitriles
• TsIm

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.