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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

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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.

Graphical abstract: 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

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Publication details

The article was received on 03 Apr 2019, accepted on 10 May 2019 and first published on 13 May 2019


Article type: Research Article
DOI: 10.1039/C9QO00468H
Org. Chem. Front., 2019, Advance Article

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    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

    K. Sun, S. Jin, S. Fang, R. Ma, X. Zhang, M. Gao, W. Zhang, T. Lu and D. Du, Org. Chem. Front., 2019, Advance Article , DOI: 10.1039/C9QO00468H

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