Preparation of 1,1´-(alkyldiyl)-bis-(2-alkylimidazole-4,5-dicarboxylic) acids

Abstract

BACKGROUND: Alkyl-bis-imidazole-4,5-dicarboxylic acids can be used both in the production of polymers with pronounced fluorescent properties and as potential antiviral agents. However, there is currently no simple method for the synthesis of alkyl-bis-imidazole-4,5-dicarboxylic acids with a wide range of substituents at both 1, 1ʹ and 2, 2ʹ positions. Therefore, the search for alternative, easier ways to synthesize compounds of this series remains relevant.

AIM: To develop a method for obtaining 2-substituted bis-imidazole-4,5-dicarboxylic acids connected at positions 1, 1ʹ by an alkyl chain of various lengths containing substituents of various lengths and nature at positions 2, 2ʹ (alkyl substituents of various lengths and heteroaryl substituents).

MATERIALS AND METHODS: Compounds of a number of bis-imidazole-4,5-dicarboxylic acids were obtained using methods of fine organic synthesis.

RESULTS: It has been shown that the oxidation of 1,1ʹ-(alkyldiyl)-bis-(2-alkylbenzimidazoles) with hydrogen peroxide in concentrated sulfuric acid leads to the production of targeted 1,1ʹ-(alkyldiyl)-bis-(2-alkylimidazole-4,5-dicarboxylic acids) in preparative quantities.

CONCLUSIONS: A new preparative method has been proposed for the preparation of 1,1ʹ-(alkyldiyl)-bis-(2-alkylimidazole-4,5-dicarboxylic acids).

Keywords

imidazole-4,5-dicarboxylic acid / 1,1ʹ-(alkyldiyl)-bis-(2-alkylimidazole-4,5-dicarboxylic acids) / oxidation / method development

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