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SYNTHESIS OF IMIDAZO[1,2-a]INDOLES FROM 2-CHLOROINDOLE-3-CARBALDEHYDE

Konstantin F. Suzdalev, Natalia I. Vikrischuk, Kseniya A. Prikhodko, Elena Y. Shasheva, Sergey V. Kurbatov, Saida K. Bogus, Pavel A. Galenko-Yaroshevsky
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Abstract


A two-step approach towards the synthesis of imidazo[1,2-a]indoles from 2-chloroindole-3-carbaldehyde has been developed. It comprises the N-alkylation of indole ring by 2-bromo-1,1-diethoxyethane followed by a treatment with aromatic amine hydrochlorides. The reaction proceeds as a nucleophilic substitution of the chlorine atom at position 2 of the indole ring followed by cyclization along with the condensation at the aldehyde group. Imidazo[1,2-a]indoles were isolated as protonated Schiff bases. Their structure was proved by 1H and 13C NMR spectroscopy and X-ray structural analysis.

Keywords


2-bromo-1,1-diethoxyethane; 2-chloroindole-3-carbaldehyde; imidazo[1,2-a]indoles; indoles,; cyclization

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