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A highly diastereoselective one-pot three-component 1,3-dipolar cycloaddition of cyclopropenes with azomethine ylides generated from 11H-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.

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

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Publication details

The article was received on 29 Sep 2017, accepted on 31 Oct 2017 and first published on 01 Nov 2017


Article type: Research Article
DOI: 10.1039/C7QO00888K
Citation: Org. Chem. Front., 2018, Advance Article
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    A highly diastereoselective one-pot three-component 1,3-dipolar cycloaddition of cyclopropenes with azomethine ylides generated from 11H-indeno[1,2-b]-quinoxalin-11-ones

    A. S. Filatov, N. A. Knyazev, M. N. Ryazantsev, V. V. Suslonov, A. G. Larina, A. P. Molchanov, R. R. Kostikov, V. M. Boitsov and A. V. Stepakov, Org. Chem. Front., 2018, Advance Article , DOI: 10.1039/C7QO00888K

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