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

Weitao Yan; Ruo Wang; Tesen Zhang; Hongtao Deng; Jian Chen; Wei Wu; Zhiqiang Weng

doi:10.1039/c8ob02701c

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

Org Biomol Chem. 2018 Dec 12;16(48):9440-9445. doi: 10.1039/c8ob02701c.

Authors

Weitao Yan¹, Ruo Wang, Tesen Zhang, Hongtao Deng, Jian Chen, Wei Wu, Zhiqiang Weng

Affiliation

¹ State Key Laboratory of Photocatalysis on Energy and Environment, College of Chemistry, Fuzhou University, Fuzhou 350108, China. zweng@fzu.edu.cn.

PMID: 30515497
DOI: 10.1039/c8ob02701c

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.

Publication types

Research Support, Non-U.S. Gov't