Abstract

A series of 5(6)-nitro- 1H -benzimidazole and their hydrazide derivatives were synthesized starting from iminoester hydrochloride and 4-nitro- o -phenylenediamine under microwave irradiation. The structure of all synthesized compounds was confirmed by IR, 1 H-NMR, 13 C-NMR, ESI-MS spectroscopy and elemental analysis. KEY WORDS : Benzimidazole, Iminoester hydrochloride, Microwave irradiation, Hydrazine hydrate Bull. Chem. Soc. Ethiop. 2013 , 27(2), 265-271. DOI: http://dx.doi.org/10.4314/bcse.v27i2.11

Highlights

  • Benzimidazoles are crucial structures for medicinal chemistry because they show important biological and pharmaceutical activities including anti-cancer, anti-microbial, anti-fungal, antiulcer and anti-viral [1, 2]

  • Various kinds of benzimidazole derivatives are found in diverse array of compounds, including biologically and therapeutically active agents [3], natural products [4]

  • A number of synthetic methods have been developed in recent years to bring out new reagents for the synthesis of 2-substitued benzimidazoles [5,6,7,8,9]

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Summary

Introduction

Benzimidazoles are crucial structures for medicinal chemistry because they show important biological and pharmaceutical activities including anti-cancer, anti-microbial, anti-fungal, antiulcer and anti-viral [1, 2]. We wish to report the synthesis of 5-nitro-1H-benzimidazoles and their hydrazide derivatives starting from iminoester hydrochlorides, which can be obtained, under microwave irradiation and with conventional heating. There has been developed a simple method using 4-nitro-o-phenylenediamine and ethylimidobenzylacetate hydrochlorides 1(a-d) Ethyl [2-benzyl-5(6)-nitro-1H-benzimidazol-1-yl]acetates 3(a-d) have been prepared with treatment of compounds 2(a-d) and ethyl bromoacetate in acetone.

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