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

Author:
Wang, Shun, Guo, Yong-Qiang, Ren, Zhi-Hui, Wang, Yao-Yu, Guan, Zheng-Hui
Source:
Organic letters 2017 v.19 no.7 pp. 1574-1577
ISSN:
1523-7052
Subject:
Lewis bases, chemical reactions, moieties, oximes
Abstract:
A novel K₂CO₃-mediated cyclization and rearrangement of γ,δ-alkynyl oximes for the synthesis of pyridols is described. The process accomplishes an efficient [1,3] rearrangement of the O-vinyl oxime intermediate which is in situ generated from the intramolecular nucleophilic addition of γ,δ-alkynyl oximes. The reaction employs readily accessible starting materials, tolerates a wide range of functional groups, and gives a variety of synthetically challenging pyridols in good yields.
Agid:
5793859