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.

Александр Сергеевич Филатов, Николай Александрович Князев, Михаил Николаевич Рязанцев, Виталий Валерьевич Суслонов, Анна Геннадьевна Ларина, Александр Павлович Молчанов, Рафаэль Равилович Костиков, Виталий Михайлович Бойцов, Александр Владимирович Степаков

Результат исследований: Научные публикации в периодических изданияхстатья

20 Цитирования (Scopus)

Аннотация

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.

Язык оригиналаанглийский
Страницы (с-по)595-605
Число страниц11
ЖурналOrganic Chemistry Frontiers
Том5
Номер выпуска4
DOI
СостояниеОпубликовано - 21 фев 2018

Предметные области Scopus

  • Органическая химия

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