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Jun 30, 2019;4 (6): 10534-10538.

Environmentally Benign, Base-Promoted Selective Amination of Polyhalogenated Pyridines.

Chao Sun, Wubing Yao, Xu Chen, Yiwen Zhao, Qiqi Wei, Zishuang Chen, Jiashou Wu, Feiyue Hao, Huiping Xie
Author Information
  1. Chao Sun: School of Pharmaceutical and Materials Engineering, Taizhou University, Jiaojiang 318000, China.
  2. Wubing Yao: School of Pharmaceutical and Materials Engineering, Taizhou University, Jiaojiang 318000, China.
  3. Xu Chen: School of Pharmaceutical and Materials Engineering, Taizhou University, Jiaojiang 318000, China.
  4. Yiwen Zhao: School of Pharmaceutical and Materials Engineering, Taizhou University, Jiaojiang 318000, China.
  5. Qiqi Wei: School of Pharmaceutical and Materials Engineering, Taizhou University, Jiaojiang 318000, China.
  6. Zishuang Chen: School of Pharmaceutical and Materials Engineering, Taizhou University, Jiaojiang 318000, China.
  7. Jiashou Wu: School of Pharmaceutical and Materials Engineering, Taizhou University, Jiaojiang 318000, China.
  8. Feiyue Hao: School of Pharmaceutical and Materials Engineering, Taizhou University, Jiaojiang 318000, China.
  9. Huiping Xie: Zhejiang Hisoar Pharmaceutical Company Limited, Taizhou 318000, PR China.
PMID: 31460151 DOI: 10.1021/acsomega.9b01031

Abstract

An environmentally benign, highly efficient, and base-promoted selective amination of various polyhalogenated pyridines including the challenging pyridine chlorides to 2-aminopyridine derivatives using water as solvent has been developed. Featuring the use of the new method, the reaction is extended to the transformation on a large scale. Mechanistic studies indicate that the pathway involving a base aidant dissociation of ,-dimethylformamide to generate dimethylamine is likely.

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