Issue 5, 2018

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

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

Supplementary files

Article information

Article type
Research Article
Submitted
02 10 2017
Accepted
13 11 2017
First published
14 11 2017

Org. Chem. Front., 2018,5, 753-759

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, 5, 753 DOI: 10.1039/C7QO00899F

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