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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 47, 2017 - Issue 9
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Original Articles

Solvent and substituent effects on the conversion of 4-methoxypyridines to N-methyl-4-pyridones

Xiao YiCollege of Pharmaceutical Science, Zhejiang Chinese Medical University, Hangzhou, P. R. China
,
Jing ChenCollege of Pharmaceutical Science, Zhejiang Chinese Medical University, Hangzhou, P. R. China
,
Xiuling XuCollege of Pharmaceutical Science, Zhejiang Chinese Medical University, Hangzhou, P. R. China
&
Yongmin MaCollege of Pharmaceutical Science, Zhejiang Chinese Medical University, Hangzhou, P. R. ChinaCorrespondence[email protected]
Pages 872-877 | Received 31 Oct 2016, Published online: 17 Mar 2017
 
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ABSTRACT

In the reaction of 4-methoxypyridine derivatives with alkyl iodides in the presence or absence of solvent, not only the pyridinium ions but also the related 1-methylpyridones are produced. The presence of solvent favors the formation of the 1-methylpyridone. Electron withdrawing groups on the pyridine ring also favor this conversion. A possible mechanism is presented.

GRAPHICAL ABSTRACT

Acknowledgments

The financial support from Zhejiang Provincial Natural Science Foundation of China (LY17H300005) and Zhejiang Chinese Medical University (2015ZG15) is gratefully acknowledged.

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