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Synthesis of 2,3-Dihydro-1H-azepine and 1H-Azepin-2(3H)-one Derivatives From Intramolecular Condensation between Stable Tertiary Enamides and Aldehydes

Wenju Zhu, Liang Zhao and Mei-Xiang Wang*

*MOE Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology, Department of Chemistry, Tsinghua University, Beijing, 100084, China, Email: wangmxmail.tsinghua.edu.cn

W. Zhu, L. Zhao, M.-X. Wang, J. Org. Chem., 2015, 80, 12047-12057.

DOI: 10.1021/acs.joc.5b02021 (free Supporting Information)


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Abstract

Under very mild conditions employing BBr3 as a Lewis acid catalyst and P2O5 as an additive, tertiary enamides that contain a formyl group underwent highly efficient and scalable intramolecular cyclic condensation to afford diverse 2,3-dihydro-1H-azepine and 1H-azepin-2(3H)-one derivatives in very good yields.

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Key Words

N-heterocycles


ID: J42-Y2015