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Synthesis 2019; 51(20): 3875-3882
DOI: 10.1055/s-0037-1610725
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© Georg Thieme Verlag Stuttgart · New York

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

Yejun Gao
a   School of Pharmaceutical and Chemical Engineering, Taizhou University, Taizhou 318000, P. R. China   Email: cre@tzc.edu.cn   Email: yongmin.ma@tzc.edu.cn
b   School of Pharmaceutical Science, Zhejiang Chinese Medical University, Hangzhou 310053, P. R. China
,
Rener Chen∗
a   School 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∗
a   School of Pharmaceutical and Chemical Engineering, Taizhou University, Taizhou 318000, P. R. China   Email: cre@tzc.edu.cn   Email: yongmin.ma@tzc.edu.cn
b   School of Pharmaceutical Science, Zhejiang Chinese Medical University, Hangzhou 310053, P. R. China
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Publication History

Received: 05 June 2019

Accepted after revision: 24 July 2019

Publication Date:
08 August 2019 (online)

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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

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610725.
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