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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 37, 2007 - Issue 13
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Original Articles

Unexpected Regiospecific Reduction of the Double Bond by NaBH4 in 2‐(1‐Methyl/1H‐benzimidazole‐2‐yl)‐3‐aryl‐acrylonitrile

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Pages 2259-2266 | Received 15 Nov 2006, Published online: 03 Jul 2007
 

Abstract

Condensation of (1H‐benzimidazole‐2‐yl)‐acetonitrile 1 with aromatic aldehydes in 5% NaOH solution gave the corresponding 2‐(1H‐benzimidazole‐2‐yl)‐3‐aryl‐acrylonitrile 2, which on treatment with NaBH4 in ethanol unexpectedly gave 2‐(1H‐benzimidazole‐2‐yl)‐3‐aryl‐propionitrile 3 by the regiospecific reduction of the double bond. Shaking a solution of 2 with H2/Pd‐C in methanol also gave 3. Reaction of 2 with DMS gave the corresponding N‐methylated analogue 5, which also with NaBH4 gave 6, once again by the regiospecific reduction of the double bond as in the case of 1‐demethylated analogue (i.e., 2).

Acknowledgment

The authors are highly indebted to the University Grants Commission (UGC), Govternment of India, New Delhi, for financial support in the form of a major research project grant.

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