Issue 48, 2018

Synthesis of 4-trifluoromethyl 2-pyrones and pyridones through the Brønsted base-catalyzed Pechmann-type reaction with cyclic 1,3-diones

Abstract

An efficient method for the synthesis of 4-trifluoromethyl 2-pyrones through the Brønsted base-catalyzed Pechmann-type reaction of cyclic 1,3-diones with ethyl 4,4,4-trifluoroacetoacetate is described. In the presence of 2-dimethylamino pyridine (2-DMAP) as a catalyst, the resulting 4-trifluoromethyl 2-pyrones are formed in good to excellent yields. Additionally, the reaction also provides 4-trifluoromethyl 2-pyridones by using the easily available NH4OAc as a source of NH3.

Graphical abstract: Synthesis of 4-trifluoromethyl 2-pyrones and pyridones through the Brønsted base-catalyzed Pechmann-type reaction with cyclic 1,3-diones

Supplementary files

Article information

Article type
Paper
Submitted
31 10 2018
Accepted
27 11 2018
First published
27 11 2018

Org. Biomol. Chem., 2018,16, 9440-9445

Synthesis of 4-trifluoromethyl 2-pyrones and pyridones through the Brønsted base-catalyzed Pechmann-type reaction with cyclic 1,3-diones

W. Yan, R. Wang, T. Zhang, H. Deng, J. Chen, W. Wu and Z. Weng, Org. Biomol. Chem., 2018, 16, 9440 DOI: 10.1039/C8OB02701C

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