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.

Standard

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

в: Organic Chemistry Frontiers, Том 5, № 4, 21.02.2018, стр. 595-605.

Результаты исследований: Научные публикации в периодических изданиях › статья › Рецензирование

BibTeX

@article{0092b609dfa0483f9ced363ec4258748,

title = "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.",

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.",

keywords = "CARBONYL YLIDES, CASTANOSPERMINE, CHEMISTRY, DERIVATIVES, EASY ACCESS, ENANTIOSELECTIVE CONSTRUCTION, KINASE INHIBITORS, PYRROLIZIDINE ALKALOIDS, SPIRO-HETEROCYCLES, STEREOSELECTIVE-SYNTHESIS",

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

year = "2018",

month = feb,

day = "21",

doi = "10.1039/c7qo00888k",

language = "English",

volume = "5",

pages = "595--605",

journal = "Organic Chemistry Frontiers",

issn = "2052-4110",

publisher = "Royal Society of Chemistry",

number = "4",

}

RIS

TY - JOUR

T1 - 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.

AU - Филатов, Александр Сергеевич

AU - Князев, Николай Александрович

AU - Рязанцев, Михаил Николаевич

AU - Суслонов, Виталий Валерьевич

AU - Ларина, Анна Геннадьевна

AU - Молчанов, Александр Павлович

AU - Костиков, Рафаэль Равилович

AU - Бойцов, Виталий Михайлович

AU - Степаков, Александр Владимирович

PY - 2018/2/21

Y1 - 2018/2/21

N2 - 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.

AB - 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.

KW - CARBONYL YLIDES

KW - CASTANOSPERMINE

KW - CHEMISTRY

KW - DERIVATIVES

KW - EASY ACCESS

KW - ENANTIOSELECTIVE CONSTRUCTION

KW - KINASE INHIBITORS

KW - PYRROLIZIDINE ALKALOIDS

KW - SPIRO-HETEROCYCLES

KW - STEREOSELECTIVE-SYNTHESIS

UR - http://www.scopus.com/inward/record.url?scp=85042106476&partnerID=8YFLogxK

UR - http://www.mendeley.com/research/highly-diastereoselective-onepot-threecomponent-13dipolar-cycloaddition-cyclopropenes-azomethine-yli

U2 - 10.1039/c7qo00888k

DO - 10.1039/c7qo00888k

M3 - Article

VL - 5

SP - 595

EP - 605

JO - Organic Chemistry Frontiers

JF - Organic Chemistry Frontiers

SN - 2052-4110

IS - 4

ER -

ID: 9282391