Abstract
The one-pot three-component reactions of 1-substituted benzimidazoles with ethyl bromoacetate and electron-deficient alkynes, in 1,2-epoxybutane, gave a variety of pyrrolo[1,2-a]quinoxalin-4-ones and pyrrolo[1,2-a]benzimidazoles. The influence of experimental conditions on the course of reaction was investigated. A novel synthetic pathway starting from benzimidazoles unsubstituted at the five membered ring, alkyl bromoacetates and non-symmetrical electron-deficient alkynes in the molar ratio of 1:2:1, in 1,2-epoxybutane at reflux temperature, led directly to pyrrolo[1,2-a]quinoxalin-4-ones in fair yield by an one-pot three-component reaction.
Highlights
The pyrrolo[1,2-a]quinoxaline system has significant biological activities and is a subject fo constant interest
We developed a selective one-pot three-component synthetic pathway towards pyrrolo[1,2-a]quinoxalin-4-one derivatives starting from benzimidazole derivatives unsubstituted at the five membered ring, alkyl bromoacetates and non-symmetrical electron-deficient alkynes in the molar ratio of 1:2:1, in 1,2-epoxybutane at reflux temperature
The high performance liquid chromatography (HPLC) analysis of crude reaction products indicated that small amounts of pyrrolo[1,2-a]benzimidazoles 5 were formed in all reactions, but they could not be always isolated from the reaction mixtures
Summary
The pyrrolo[1,2-a]quinoxaline system has significant biological activities and is a subject fo constant interest. Our interest in developing simple synthetic pathways towards N-bridged heterocyclic compounds [17,18,19,20] prompted us to investigate the one-pot three-component reactions of various substituted benzimidazoles with alkyl bromoacetates and electron-deficient alkynes in presence of an epoxide.
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