A highly diastereoselective one-pot three-component 1,3-dipolar cycloaddition of cyclopropenes with azomethine ylides generated from 11 H -indeno[1,2- b] -quinoxalin-11-ones

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Abstract

A simple and efficient method has been developed for the synthesis of complex compounds with spiro-fused 11H-indeno[1,2-b]quinoxaline and cyclopropa[a]pyrrolizine or azabicyclo[3.1.0]hexane moieties. All the products have been synthesized in good to high yields and excellent diastereoselectivity by one-pot three-component 1,3-dipolar cycloaddition reactions of various derivatives of cyclopropene with azomethine ylides. Azomethine ylides were in situ generated from 11H-indeno[1,2-b]quinoxalin-11-one derivatives and amines, such as N-substituted and N-unsubstituted α-amino acids, benzylamines, and also peptides (dipeptide Gly-Gly and tripeptide Gly-Gly-Gly). To understand the mechanism that allows for azomethine ylide generation followed by 1,3-dipolar cycloaddition, a quantum chemical investigation was performed. The anticancer activity of some of the obtained compounds against the human leukemia K562 cell line was evaluated by flow cytometry in vitro.

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Filatov, A. S., Knyazev, N. A., Ryazantsev, M. N., Suslonov, V. V., Larina, A. G., Molchanov, A. P., … Stepakov, A. V. (2018). A highly diastereoselective one-pot three-component 1,3-dipolar cycloaddition of cyclopropenes with azomethine ylides generated from 11 H -indeno[1,2- b] -quinoxalin-11-ones. Organic Chemistry Frontiers, 5(4), 595–605. https://doi.org/10.1039/c7qo00888k

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