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DOI: 10.1055/a-2676-4508
Unusual Reductive Cyclization of 3-Nitro-4-(phenylamino)benzoic acid: Benzimidazole instead of Phenazine
This publication has been supported by RUDN University Scientific Projects Grant System, project № 021411–0–000. The authors are grateful for carrying out X-ray diffraction measurements for X-ray structural analysis on a single-crystal X-ray diffractometer Stoe STADI VARI PILATUS, purchased as part of the Development Program of Lomonosov Moscow State University [1832-2011]
Abstract
It is known that o-nitroanilines undergo cyclization to form phenazines in the presence of sodium borohydride under basic conditions. We have shown that under similar conditions, 3-nitro-4-(phenylamino)benzoic acid 1a cyclizes to 2-alkyl-1-phenylbenzimidazole-5-carboxylic acids. 2-Methyl-substituted benzimidazole crystallizes to form crystals of its mixed salts with NaCl and HCl, as characterized by X-ray data. Sodium alkoxide acts as a reducing agent for the nitro group of the initial o-nitroaniline in the reaction. Based on the obtained results, a possible reaction mechanism has been proposed.
Data Availability
Data are available on request.
Publication History
Received: 17 April 2025
Accepted after revision: 04 August 2025
Article published online:
21 August 2025
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