Specific N‑Alkylation of Hydroxypyridines Achieved by a Catalyst- and Base-Free Reaction with Organohalides

A specific N-alkylation of 2-hydroxypyridines is achieved by reacting with organohalides under catalyst- and base-free conditions. The observed HX-facilitated conversion of pyridyl ether intermediates to 2-pyridone products may account for the success and specific N-alkylation of the reaction under...

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Bibliographic Details
Published in:Journal of organic chemistry 2018-06, Vol.83 (12), p.6769-6775
Main Authors: Feng, Bin, Li, Yang, Li, Huan, Zhang, Xu, Xie, Huamei, Cao, Hongen, Yu, Lei, Xu, Qing
Format: Article
Language:English
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Summary:A specific N-alkylation of 2-hydroxypyridines is achieved by reacting with organohalides under catalyst- and base-free conditions. The observed HX-facilitated conversion of pyridyl ether intermediates to 2-pyridone products may account for the success and specific N-alkylation of the reaction under the unexpectedly simple conditions. This new reaction may provide a useful alternative for the synthesis of 2-pyridones and analogous structures because of its >99% N-selectivity, relatively broad scopes of both substrates, and no mandatory use of catalysts and bases.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.8b00787