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Cascade reaction of alkynols with 1-(2-aminophenyl)prop-2-ynols to form a fused 5,5,6-tricyclic system: formation of four bonds in a single reaction

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Abstract

A novel cascade reaction of internal alkynols with 1-(2-aminophenyl)prop-2-ynols has been developed to form a new N,O-containing fused 5,5,6-tricyclic skeleton. Mechanistic studies indicate that this reaction proceeds via alkynol cycloisomerization, intermolecular substitution with 1-(2-aminophenyl)prop-2-ynols, and intermolecular addition with alkynols and consequent cyclizations. In this way, two C–C bonds, one C–O bond and one C–N bond form to give a tricyclic skeleton in a single reaction.

Graphical abstract: Cascade reaction of alkynols with 1-(2-aminophenyl)prop-2-ynols to form a fused 5,5,6-tricyclic system: formation of four bonds in a single reaction

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Publication details

The article was received on 28 May 2017, accepted on 10 Jul 2017 and first published on 10 Jul 2017


Article type: Communication
DOI: 10.1039/C7CC04126H
Citation: Chem. Commun., 2017, Advance Article
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    Cascade reaction of alkynols with 1-(2-aminophenyl)prop-2-ynols to form a fused 5,5,6-tricyclic system: formation of four bonds in a single reaction

    X. Mao, X. Zhu, D. Li, L. Jiang and P. Liu, Chem. Commun., 2017, Advance Article , DOI: 10.1039/C7CC04126H

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