Synthesis of Asymmetrical 2,6-Diarylpyridines from Linear α,β,γ,δ-Unsaturated Ketones by Addition of Ammonium Formate Followed by Annulation

Yejun Gao; Rener Chen; Yongmin Ma

doi:10.1055/s-0037-1610725

Synthesis, Table of Contents

Synthesis 2019; 51(20): 3875-3882
DOI: 10.1055/s-0037-1610725

paper

Synthesis of Asymmetrical 2,6-Diarylpyridines from Linear α,β,γ,δ-Unsaturated Ketones by Addition of Ammonium Formate Followed by Annulation

Yejun Gao

^aSchool of Pharmaceutical and Chemical Engineering, Taizhou University, Taizhou 318000, P. R. China Email: cre@tzc.edu.cn Email: yongmin.ma@tzc.edu.cn

^bSchool of Pharmaceutical Science, Zhejiang Chinese Medical University, Hangzhou 310053, P. R. China

,

Rener Chen∗

^aSchool of Pharmaceutical and Chemical Engineering, Taizhou University, Taizhou 318000, P. R. China Email: cre@tzc.edu.cn Email: yongmin.ma@tzc.edu.cn

,

Yongmin Ma∗

^aSchool of Pharmaceutical and Chemical Engineering, Taizhou University, Taizhou 318000, P. R. China Email: cre@tzc.edu.cn Email: yongmin.ma@tzc.edu.cn

^bSchool of Pharmaceutical Science, Zhejiang Chinese Medical University, Hangzhou 310053, P. R. China

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Abstract

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In memory of Professor Yongmin Zhang (1932–2019)

Abstract

A simple and efficient method has been established for the synthesis of asymmetrical 2,6-diarylpyridines by cyclization of α,β,γ,δ-unsaturated ketones with ammonium formate under air atmosphere. The reaction is metal-free and operationally convenient from readily available starting materials. Thirty-three examples have been presented, most of which show good yields.

Key words

regioselectivity - Michael addition - annulations - 2,4-dien-1-one - asymmetrical pyridine

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References

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