Synthesis of 2,3,5,6-Tetrasubstituted Pyridines via Copper-Catalyzed Domino Oxidative Annulation of 1,3-Dicarbonyl Compounds with Methanol and Ammonium Acetate

doi:10.6023/cjoc201807003

Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (12): 3381-3385.DOI: 10.6023/cjoc201807003 Previous Articles Next Articles

Notes

铜催化的1,3-二羰基化合物、甲醇和乙酸铵的串联氧化环化合成2,3,5,6-四取代吡啶

闫溢哲^a,b, 李政^a, 崔畅^a, 刘延奇^a

a 郑州轻工业学院食品与生物工程学院郑州 450000;
b 食品生产与安全河南省协同创新中心郑州 450000

收稿日期:2018-07-01 修回日期:2018-07-12 发布日期:2018-08-22
通讯作者: 闫溢哲, 刘延奇 E-mail:yanyizhe@mail.ustc.edu.cn;liuyanqi@zzuli.edu.cn
基金资助:
国家自然科学基金（No.21502177）、河南省科技攻关计划（No.182102310903）、郑州轻工业学院博士研究基金（No.2014BSJJ032）和郑州轻工业学院青年骨干教师资助项目.

Synthesis of 2,3,5,6-Tetrasubstituted Pyridines via Copper-Catalyzed Domino Oxidative Annulation of 1,3-Dicarbonyl Compounds with Methanol and Ammonium Acetate

Yan Yizhe^a,b, Li Zheng^a, Cui Chang^a, Liu Yanqi^a

a School of Food and Biological Engineering, Zhengzhou University of Light Industry, Zhengzhou 450000;
b Collaborative Innovation Center of Food Production and Safety, Henan 450000

Received:2018-07-01 Revised:2018-07-12 Published:2018-08-22
Contact: 10.6023/cjoc201807003 E-mail:yanyizhe@mail.ustc.edu.cn;liuyanqi@zzuli.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21502177), the Scientific and Technological Breakthrough Plan of Henan Province (No. 182102310903), the Doctoral Research Foundation of Zhengzhou University of Light Industry (No. 2014BSJJ032), and the Grants Program of Youth Backbone Teachers Training Object of Zhengzhou University of Light Industry.

1. Synthesis of 2,3,5,6-Tetrasubstituted Pyridines via Copper-Catalyzed Domino Oxidative Annulation of 1,3-Dicarbonyl Compounds with Methanol and Ammonium Acetate.PDF(4080KB)

Abstract

A copper-catalyzed oxidative formal cycloaddition of 1,3-dicarbonyl compounds, methanol and ammonium acetate was first demonstrated, affording symmetrical 2,3,5,6-tetrasubstituted pyridines in moderate to excellent yields. Methanol was employed as the carbon synthon as well as the reaction solvent. The preliminary mechanistic studies revealed that the reaction underwent a radical pathway and the C(sp³)-H bond cleavage of methanol was the rate-determining step. This method is operationally simple and environmentally friendly.

Key words: copper, oxidative annulation, pyridine, methanol

Cite this article

Yan Yizhe, Li Zheng, Cui Chang, Liu Yanqi. Synthesis of 2,3,5,6-Tetrasubstituted Pyridines via Copper-Catalyzed Domino Oxidative Annulation of 1,3-Dicarbonyl Compounds with Methanol and Ammonium Acetate[J]. Chin. J. Org. Chem., 2018, 38(12): 3381-3385.

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铜催化的1,3-二羰基化合物、甲醇和乙酸铵的串联氧化环化合成2,3,5,6-四取代吡啶

Synthesis of 2,3,5,6-Tetrasubstituted Pyridines via Copper-Catalyzed Domino Oxidative Annulation of 1,3-Dicarbonyl Compounds with Methanol and Ammonium Acetate

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