73724-11-5Relevant academic research and scientific papers
Unexpected regiospecific reduction of the double bond by NaBH4 in 2-(1-methyl/1H-benzimidazole-2-yl)-3-aryl-acrylonitrile
Dubey,Reddy, P. V. V. Prasada
, p. 2259 - 2266 (2007)
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). Copyright Taylor & Francis Group, LLC.
