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

作者：Filatov A S; Knyazev N A; Ryazantsev M N; Suslonov V V; Larina A G; Molchanov A P; Kostikov R R; Boitsov V M; Stepakov A V

来源：Organic Chemistry Frontiers, 2018, 5(4): 595-605.

DOI：10.1039/c7qo00888k

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 alpha-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.

• 出版日期2018-2-21