Copper-Catalyzed Reaction of Secondary Propargylamines with Ethyl Buta-2,3-dienoate for the Synthesis of 1,6-Dihydropyridines

Chao Liu; Gaigai Wang; Yuqing Wang; Olga P. Pereshivko; Vsevolod A. Peshkov

doi:10.1002/ejoc.201801227

Copper-Catalyzed Reaction of Secondary Propargylamines with Ethyl Buta-2,3-dienoate for the Synthesis of 1,6-Dihydropyridines

Chao Liu
, Gaigai Wang
, Yuqing Wang
, Olga P. Pereshivko
, Vsevolod A. Peshkov

Soochow University
Suzhou Key Laboratory of Green Chemical Engineering

Результат исследований › рецензирование

12 Цитирования (Scopus)

Аннотация

A copper(I) bromide-catalyzed reaction of A ³ -coupling-derived propargylamines with ethyl buta-2,3-dienoate for the fast assembly of a 1,6-dihydropyridine core is described. The developed protocol was tested on a variety of secondary propargylamines and the possibility of a one-pot synthesis of 1,6-dihydropyridine through the A ³ -coupling and subsequent ethyl buta-2,3-dienoate incorporation was investigated.

Язык оригинала	English
Страницы (с-по)	1981-1985
Число страниц	5
Журнал	European Journal of Organic Chemistry
Том	2019
Номер выпуска	10
DOI	https://doi.org/10.1002/ejoc.201801227
Состояние	Published - мар. 14 2019

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry

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10.1002/ejoc.201801227

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title = "Copper-Catalyzed Reaction of Secondary Propargylamines with Ethyl Buta-2,3-dienoate for the Synthesis of 1,6-Dihydropyridines",

abstract = " A copper(I) bromide-catalyzed reaction of A 3 -coupling-derived propargylamines with ethyl buta-2,3-dienoate for the fast assembly of a 1,6-dihydropyridine core is described. The developed protocol was tested on a variety of secondary propargylamines and the possibility of a one-pot synthesis of 1,6-dihydropyridine through the A 3 -coupling and subsequent ethyl buta-2,3-dienoate incorporation was investigated. ",

keywords = "Allenes, Copper, Cyclization, Dihydropyridines, Propargylamines",

author = "Chao Liu and Gaigai Wang and Yuqing Wang and Pereshivko, \{Olga P.\} and Peshkov, \{Vsevolod A.\}",

note = "Funding Information: This work was supported by the start-up fund from Soochow University (grant Q410900714), National Natural Science Foundation of China (grant 21650110445), Natural Science Foundation of Jiangsu Province of China (grants BK20160310 and BK20150317), the Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD) and the Project of Scientific and Technologic Infrastructure of Suzhou (grant SZS201708). Publisher Copyright: {\textcopyright} 2019 WILEY-VCH Verlag GmbH \& Co. KGaA, Weinheim",

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doi = "10.1002/ejoc.201801227",

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T1 - Copper-Catalyzed Reaction of Secondary Propargylamines with Ethyl Buta-2,3-dienoate for the Synthesis of 1,6-Dihydropyridines

AU - Liu, Chao

AU - Wang, Gaigai

AU - Wang, Yuqing

AU - Pereshivko, Olga P.

AU - Peshkov, Vsevolod A.

N1 - Funding Information: This work was supported by the start-up fund from Soochow University (grant Q410900714), National Natural Science Foundation of China (grant 21650110445), Natural Science Foundation of Jiangsu Province of China (grants BK20160310 and BK20150317), the Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD) and the Project of Scientific and Technologic Infrastructure of Suzhou (grant SZS201708). Publisher Copyright: © 2019 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

PY - 2019/3/14

Y1 - 2019/3/14

N2 - A copper(I) bromide-catalyzed reaction of A 3 -coupling-derived propargylamines with ethyl buta-2,3-dienoate for the fast assembly of a 1,6-dihydropyridine core is described. The developed protocol was tested on a variety of secondary propargylamines and the possibility of a one-pot synthesis of 1,6-dihydropyridine through the A 3 -coupling and subsequent ethyl buta-2,3-dienoate incorporation was investigated.

AB - A copper(I) bromide-catalyzed reaction of A 3 -coupling-derived propargylamines with ethyl buta-2,3-dienoate for the fast assembly of a 1,6-dihydropyridine core is described. The developed protocol was tested on a variety of secondary propargylamines and the possibility of a one-pot synthesis of 1,6-dihydropyridine through the A 3 -coupling and subsequent ethyl buta-2,3-dienoate incorporation was investigated.

KW - Allenes

KW - Copper

KW - Cyclization

KW - Dihydropyridines

KW - Propargylamines

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UR - https://www.scopus.com/pages/publications/85057501034#tab=citedBy

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JF - European Journal of Organic Chemistry

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