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Synthesis of Polysubstituted Pyridines via a One-Pot Metal-Free Strategy

Hongbo Wei, Yun Li*, Ke Xiao, Bin Cheng, Huifei Wang, Lin Hu and Hongbin Zhai*

*The State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engeneering, Lanzhou University, Lanzhou 730000, China, Email: liyunlzu.edu.cn, zhaihlzu.edu.cn

H. Wei, Y. Li, K. Xiao, B. Cheng, H. Wang, L. Hu, H. Zhai, Org. Lett., 2015, 17, 5974-5977.

DOI: 10.1021/acs.orglett.5b02903 (free Supporting Information)


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Abstract

A reaction sequence involving a Wittig reaction, a Staudinger reaction, an aza-Wittig reaction, a 6π-3-azatriene electrocyclization, and a 1,3-H shift enables a quick one-pot synthesis of polysubstituted pyridines in very good yields from aldehydes, phosphorus ylides, and propargyl azide.

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Key Words

pyridines, Wittig reaction, Staudinger reaction, triphenylphosphine


ID: J54-Y2015