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.
CITATION STYLE
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
Mendeley helps you to discover research relevant for your work.