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NEW METHOD FOR THE SYNTHESIS OF 2-SUBSTITUTED BENZIMIDAZOLE-5(6)-CARBOXYLIC ACIDS

Вахид А. Мамедов, Наталья А. Жукова, Виктор В. Сякаев, Миляуша С. Кадырова, Татьяна Н. Бесчастнова, Ильдар Х. Ризванов, Шамиль К. Латыпов
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Abstract


A new method is proposed for the synthesis of 2-substituted benzimidazole-5(6)-carboxylic acids. The acid-catalyzed rearrangement of 2(3)-aroyl-3(2)-oxo-3,4(1,2)-dihydroquinoxaline-6-carboxylic acids was shown to proceed with the formation of 2-(3-arylquinoxalin-2-yl)-1H-benzimidazole-5(6)-carboxylic acids. NMR studies of the rearrangement reaction product, 2-(3-phenylquinoxalin-2-yl)-1H-benzimidazole-6-carboxylic acid, indicated that it existed as a mixture of two tautomeric forms due to benzimidazole tautomerism under the NMR conditions. The carboxyl group of the synthesized benzimidazoles was used for the preparation of new derivatives.

Authors: Vakhid A. Mamedov*, Nataliya A. Zhukova, Victor V. Syakaev, Milyausha S. Kadyrova, Tat'yana N. Beschastnova, Il'dar Kh. Rizvanov, Shamil K. Latypov


Keywords


4-aminobenzoic acid derivatives; benzimidazole-5(6)-carboxylic acids; 2,5'-bibenzimidazoles; 2-oxo-3,4-dihydroquinoxaline-6-carboxylic acids; o-phenylenediamine; Mamedov rearrangement

Full Text: PDF (Russian) Supplementary File(s): Supporting information (673KB)


 

 

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