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K2CO3-Mediated Cyclization and Rearrangement of γ,δ-Alkynyl Oximes To Form Pyridols

Shun Wang, Yong-Qiang Guo, Zhi-Hui Ren, Yao-Yu Wang and Zheng-Hui Guan*

*Key Laboratory of Synthetic and Nature Molecule Chemistry of Ministry of Education, Department of Chemistry & Materials Science, Northwest University, Xi’an 710127, P. R. China, Email: guanzhhnwu.edu.cn

S. Wang, Y.-Q. Guo, Z.-H. Ren, Y.-Y. Wang, Z.-H. Guan, Org. Lett., 2017, 19, 1574-1577.

DOI: 10.1021/acs.orglett.7b00389 (free Supporting Information)


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Abstract

A K2CO3-mediated cyclization and rearrangement of γ,δ-alkynyl oximes for the synthesis of pyridols employs readily accessible starting materials, tolerates a wide range of functional groups, and gives various synthetically challenging pyridols in good yields. The reaction proceeds via an efficient [1,3] rearrangement of an O-vinyl oxime intermediate which is in situ generated by intramolecular nucleophilic addition of γ,δ-alkynyl oximes.

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Key Words

pyridines


ID: J54-Y2017