Synlett 2019; 30(05): 605-609
DOI: 10.1055/s-0037-1612077
letter
© Georg Thieme Verlag Stuttgart · New York

One-Pot Sequential Multistep Transformation of α,β-Unsaturated Trifluoromethyl Ketones: Facile Synthesis of Trifluoromethylated 2-Pyridones

Ning Lv
a   Department of Chemistry, Tianjin Key Laboratory of Molecular Optoelectronic Sciences, and Tianjin Collaborative Innovation Centre of Chemical Science and Engineering, Tianjin University, Tianjin 300072, P. R. of China
,
Yi-Qiang Tian
a   Department of Chemistry, Tianjin Key Laboratory of Molecular Optoelectronic Sciences, and Tianjin Collaborative Innovation Centre of Chemical Science and Engineering, Tianjin University, Tianjin 300072, P. R. of China
,
a   Department of Chemistry, Tianjin Key Laboratory of Molecular Optoelectronic Sciences, and Tianjin Collaborative Innovation Centre of Chemical Science and Engineering, Tianjin University, Tianjin 300072, P. R. of China
,
Jun-An Ma*
a   Department of Chemistry, Tianjin Key Laboratory of Molecular Optoelectronic Sciences, and Tianjin Collaborative Innovation Centre of Chemical Science and Engineering, Tianjin University, Tianjin 300072, P. R. of China
b   State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, P. R. of China   Email: zhangfg1987@tju.edu.cn   Email: majun_an68@tju.edu.cn
› Author Affiliations


This work was supported financially by the National ­Natural Science Foundation of China (No. 21472137, 21532008, and 21772142) and the National Basic Research Program of China (973 Program: 2014CB745100).
Further Information

Publication History

Received: 16 October 2018

Accepted after revision: 21 December 2018

Publication Date:
23 January 2019 (online)


Abstract

A one-pot transformation of α,β-unsaturated trifluoromethyl ketones with 2-(phenylsulfinyl)acetamide to give trifluoromethylated 2-pyridones is realized. The reaction proceeds under mild conditions and involves multiple steps in an expeditious and controlled sequence to provide efficient access to a broad range of trifluoromethylated 2-pyridones in moderate to high yields. Moreover, further synthetic manipulations permit the routine synthesis of a diverse array of trifluoromethylated pyridines with good efficiency.

Supporting Information

 
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