N-Heterocyclic carbene-catalyzed formal [3 + 3] annulation of alkynoic acid esters with indolin-3-ones: access to functionalized pyrano[3,2-b]indol-2-ones
Literature Information
Publication Date
2019-05-13
DOI
10.1039/C9QO00468H
Impact Factor
5.281
Authors
Kewen Sun, Shiyi Jin, Shuaishuai Fang, Rui Ma, Xinmiao Zhang, Maoyu Gao, Wanqi Zhang, Tao Lu, Ding Du
View Original
Abstract
An N-heterocyclic carbene-catalyzed formal [3 + 3] annulation of alkynoic acid esters with indolin-3-ones has been developed for the rapid and efficient construction of the pyrano[3,2-b]indol-2-one skeleton, which is found as the core structure in numerous biologically active compounds. The catalytically generated alkynyl acylazoliums through the combination of a carbene with alkynoic acid esters proved to be the key for the success of this transformation, which enriches and explores the chemistry of alkynyl acylazolium intermediates.
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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
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4-[(3-Chloro-2-fluorophenyl)amino]-7-methoxy-6-quinazolinyl acetate
CAS Number:
740081-22-5
Molecular Formula:
C17H13ClFN3O3
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6-Bromo-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine
CAS Number:
1203499-17-5
Molecular Formula:
C7H7BrN2O
1-(3-Bromo-4-fluorophenyl)methanamine hydrochloride (1:1)
CAS Number:
202865-68-7
Molecular Formula:
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