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Thiazolium salt-catalyzed [3 + 2 + 1] cyclization for the synthesis of trisubstituted 2-pyrones using arylglyoxals as a carbonyl source

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Abstract

A new thiazolium salt-catalyzed [3 + 2 + 1] cyclization of acetylenedicarboxylates with arylglyoxals has been developed, enabling organocatalytic umpolung to access trisubstituted 2-pyrones with good yields via C–C bond cleavage, in which arylglyoxals played dual roles as a ring component as well as a carbonyl source. The reaction mechanism was proposed based on LC-MS analysis.

Graphical abstract: Thiazolium salt-catalyzed [3 + 2 + 1] cyclization for the synthesis of trisubstituted 2-pyrones using arylglyoxals as a carbonyl source

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Publication details

The article was received on 02 Oct 2017, accepted on 13 Nov 2017 and first published on 14 Nov 2017


Article type: Research Article
DOI: 10.1039/C7QO00899F
Citation: Org. Chem. Front., 2018, Advance Article
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    Thiazolium salt-catalyzed [3 + 2 + 1] cyclization for the synthesis of trisubstituted 2-pyrones using arylglyoxals as a carbonyl source

    L. Xu, P. Zhou, J. Li, W. Hao, S. Tu and B. Jiang, Org. Chem. Front., 2018, Advance Article , DOI: 10.1039/C7QO00899F

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