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

Authors

  • Вахид А. Мамедов A. E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center of the Russian Academy of Sciences, 8 Akademika Arbuzova St., Kazan 420088, Tatarstan
  • Наталья А. Жукова A. E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center of the Russian Academy of Sciences, 8 Akademika Arbuzova St., Kazan 420088, Tatarstan
  • Виктор В. Сякаев A. E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center of the Russian Academy of Sciences, 8 Akademika Arbuzova St., Kazan 420088, Tatarstan
  • Миляуша С. Кадырова A. E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center of the Russian Academy of Sciences, 8 Akademika Arbuzova St., Kazan 420088, Tatarstan
  • Татьяна Н. Бесчастнова A. E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center of the Russian Academy of Sciences, 8 Akademika Arbuzova St., Kazan 420088, Tatarstan
  • Ильдар Х. Ризванов A. E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center of the Russian Academy of Sciences, 8 Akademika Arbuzova St., Kazan 420088, Tatarstan
  • Шамиль К. Латыпов A. E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center of the Russian Academy of Sciences, 8 Akademika Arbuzova St., Kazan 420088, Tatarstan

DOI:

https://doi.org/10.1007/4023

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

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

Author Biographies

Вахид А. Мамедов, A. E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center of the Russian Academy of Sciences, 8 Akademika Arbuzova St., Kazan 420088, Tatarstan

заведующий лабораторией Химии гетеро­цик­лических соединений УРАН ИОФХ им. А.Е. Арбузова КазНЦ РАН д.х.н., профессор

Наталья А. Жукова, A. E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center of the Russian Academy of Sciences, 8 Akademika Arbuzova St., Kazan 420088, Tatarstan

к.х.н., с.н.с. лаборатории Химии гетероциклических соединений ИОФХ им. А.Е. Арбузова КазНЦ РАН

Виктор В. Сякаев, A. E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center of the Russian Academy of Sciences, 8 Akademika Arbuzova St., Kazan 420088, Tatarstan

к.х.н., с.н.с. лаборатории Радиоспектроскопии ИОФХ им. А.Е. Арбузова КазНЦ РАН

Миляуша С. Кадырова, A. E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center of the Russian Academy of Sciences, 8 Akademika Arbuzova St., Kazan 420088, Tatarstan

аспирант кафедры Органической химии Казанского национального исследовательского технологического университета

Татьяна Н. Бесчастнова, A. E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center of the Russian Academy of Sciences, 8 Akademika Arbuzova St., Kazan 420088, Tatarstan

м.н.с. лаборатории Химии гетероциклических соединений ИОФХ им. А.Е. Арбузова КазНЦ РАН

Ильдар Х. Ризванов, A. E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center of the Russian Academy of Sciences, 8 Akademika Arbuzova St., Kazan 420088, Tatarstan

заведующий лабораторией Физико-химического анализа ИОФХ им. А.Е. Арбузова КазНЦ РАН, к.х.н.

Шамиль К. Латыпов, A. E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center of the Russian Academy of Sciences, 8 Akademika Arbuzova St., Kazan 420088, Tatarstan

заведующий лабораторией Радиоспектроскопии ИОФХ им. А.Е. Арбузова КазНЦ РАН, д.х.н.

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Published

2017-11-03

Issue

Vol. 53 No. 9 (2017): Rearrangements in the chemistry of heterocycles

Section

Original Papers