Journal
SYNTHETIC COMMUNICATIONS
Volume 40, Issue 16, Pages 2429-2440Publisher
TAYLOR & FRANCIS INC
DOI: 10.1080/00397910903261395
Keywords
Aldoximes; DBU; dehydration; DMF; nitriles; TsIm
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Funding
- Shiraz University of Technology
- Shiraz University Research Councils
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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.
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