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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 40, 2009 - Issue 2
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Original Articles

Novel Zinc Ion–Catalyzed Synthesis of Unsymmetric Multisubstituted Pyridines

Qingyun Ren Key Laboratory of Pesticide and Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan, Hubei, P. R. China
,
Wenyan Mo Key Laboratory of Pesticide and Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan, Hubei, P. R. China
,
Yongyan Yao Key Laboratory of Pesticide and Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan, Hubei, P. R. China
,
Hongwu He Key Laboratory of Pesticide and Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan, Hubei, P. R. ChinaCorrespondence[email protected]
&
Yucheng Gu Key Laboratory of Pesticide and Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan, Hubei, P. R. China; Syngenta, Jealott's Hill International Research Centre, Bracknell, Berkshire, United Kingdom
Pages 303-312 | Received 20 Dec 2008, Published online: 29 Dec 2009
 
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Abstract

A facile and convenient synthesis of unsymmetric multisubstituted pyridines from β-ketoesters and ketene N,S-acetals or ketene N,N-acetals has been achieved in good yields catalyzed by Zn(NO3)2·6H2O in the presence of triethylbenzylammonium (TEBA) chloride in ethanol. This reaction was carried out under economical, one-pot reaction conditions (using easily obtained starting materials, and inexpensive catalyst and solvent) and offers considerable improvements over traditional methodology.

ACKNOWLEDGMENTS

This project was supported by the National Key Project for Basic Research Development Program of China (No. 2003CB114400), the National Natural Science Foundation of China (No. 20772042), the National Science and Technique Foundation of China (No. 2006BAE01A01-10), and Syngenta Ltd.

Notes

a Yield of pure isolated product.

a Yield of pure isolated product.

a Yield of pure isolated product.

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