SYNTHESIS AND TAUTOMERISM OF 2-PHENACYL-1<i>H</i>-BENZIMIDAZOLES AND THEIR HYDROGEN BROMIDE SALTS

Authors

  • И. Б. Дзвинчук Institute of Organic Chemistry, National Academy of Sciences of Ukraine
  • А. М. Нестеренко Institute of Organic Chemistry, National Academy of Sciences of Ukraine
  • В. В. Половинко Ukrorgsintez
  • А. Б. Рябицкий Institute of Organic Chemistry, National Academy of Sciences of Ukraine
  • М. О. Лозинский Institute of Organic Chemistry, National Academy of Sciences of Ukraine

DOI:

https://doi.org/10.1007/1411

Keywords:

benzimidazoles, acylation, deacylation, quantum-chemical study, spectroscopy, tautomerism

Abstract

2-Phenacyl-1H-benzimidazoles were prepared by the acylation of 2-methylbenzimidazole using aroyl chlorides with subsequent alcoholysis or aminolysis of the N,C,O-triacylation products obtained. Treatment of the 2-phenacyl-1H-benzimidazoles with hydrobromic acid gave the corresponding salts. The structure of the products was supported by IR, 1H and 13C NMR, and HMBC spectroscopy as well as by quantum-chemical calculations. 2-Phenacyl-1H-benzimidazoles in DMSO-d6 solution were found to display predominantly imino-enamino tautomerism, while their salts were found to display predominantly keto-enol tautomerism.

Authors: I. B. Dzvinchuk, A. M. Nesterenko, V. V. Polovinko, A. B. Ryabitskii, and M. O. Lozinskii.

English translation in Chemistry of Heterocyclic Compounds, 2011, 47 (8), pp 953-963

http://link.springer.com/article/10.1007/s10593-011-0860-7

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Published

2013-12-18

Issue

No. 8 (2011)

Section

Original Papers