4.3 Article

A COMBINED-REDOX SYNTHESIS OF 2-ALKYLBENZIMIDAZOLES FROM 2-NITROANILINES BY SEMICONDUCTOR PHOTOCATALYSIS

Journal

SYNTHETIC COMMUNICATIONS
Volume 42, Issue 10, Pages 1500-1508

Publisher

TAYLOR & FRANCIS INC
DOI: 10.1080/00397911.2010.541587

Keywords

Combined redox reaction; 1-ethyl-2-methylbenzimidazole; 2-methylbenzimidazole; photocatalytic cyclization; TiO2-P25

Funding

  1. Council of Scientific and Industrial Research, New Delhi
  2. Ministry of Environment and Forests (MOEF), New Delhi [315-F-36, 19/9/2007-RE]

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One-pot photocatalytic synthesis of 2-substituted benzimidazoles from 2-nitroanilines with different alcohols by combined redox cyclization reaction using TiO2-P25 is reported. The reaction, when performed with ethanol, gives 2-methylbenzimidazole as a single product. However, in a mixture of ethanol and water (1:1), it gives both 2-methylbenzimidazole and 1-ethyl-2-methylbenzimidazole. The products have been characterized by Fourier transorm-infrared, H-1 NMR, (CNMR)-C-13, and gas chromatography-mass spectrometry analysis. TiO2-P25 behaves as a combined redox photocatalyst by reducing 2-nitroaniline and oxidizing alcohols simultaneously under ultraviolet light. Easy product isolation under mild conditions and good yield make this one-pot synthesis ecofriendly.

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