Synthesis of 1,2,4-Triazolo[4,3-a]pyridines by I2-Catalyzed Oxidative Coupling of 2-Aminopyridines with N-Tosylhydrazones

doi:10.6023/cjoc202205040

Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (11): 3863-3869.DOI: 10.6023/cjoc202205040 Previous Articles Next Articles

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I₂催化下通过2-氨基吡啶和N-对甲苯磺酰腙氧化偶联反应合成1,2,4-三唑[4,3-a]吡啶

陈永欣^a, 郭鑫^b, 刘亚凤^b, 杨雪莹^b, 陈保华^b^,^*()

^a中国科学院西北生态环境资源研究院兰州 730000
^b兰州大学功能有机分子化学国家重点实验室兰州 730000

收稿日期:2022-05-23 修回日期:2022-06-24 发布日期:2022-07-05
通讯作者: 陈保华
基金资助:
国家自然科学基金(42002174); 甘肃省自然科学基金(20JR10RA030); 宁夏重点研发(2019BEB04028)

Synthesis of 1,2,4-Triazolo[4,3-a]pyridines by I₂-Catalyzed Oxidative Coupling of 2-Aminopyridines with N-Tosylhydrazones

Yongxin Chen^a, Xin Guo^b, Yafeng Liu^b, Xueying Yang^b, Baohua Chen^b()

^aNorthwest Institute of Eco-Environment and Resources, Chinese Academy of Sciences, Lanzhou 730000
^bState Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000

Received:2022-05-23 Revised:2022-06-24 Published:2022-07-05
Contact: Baohua Chen
Supported by:
National Natural Science Foundation of China(42002174); Natural Science Foundation of Gansu Province(20JR10RA030); Ningxia Key Research and Development Program(2019BEB04028)

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Abstract

An efficient synthesis of 1,2,4-triazolo[4,3-a]pyridines from N-tosylhydrazones and 2-aminopyridines via S—N/ C—N bond cleavage and new C—N bond formation has been developed. The procedure, using I₂ as the catalyst, is a simple, general, and efficient protocol, which could be applied to various substrates in moderate to good yields.

Key words: tert-butyl hydroperoxide (TBHP), 2-aminopyridine, N-tosylhydrazone, cyclization, 1,2,4-triazolo[4,3-a]pyridine

Cite this article

Yongxin Chen, Xin Guo, Yafeng Liu, Xueying Yang, Baohua Chen. Synthesis of 1,2,4-Triazolo[4,3-a]pyridines by I₂-Catalyzed Oxidative Coupling of 2-Aminopyridines with N-Tosylhydrazones[J]. Chinese Journal of Organic Chemistry, 2022, 42(11): 3863-3869.

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I₂催化下通过2-氨基吡啶和N-对甲苯磺酰腙氧化偶联反应合成1,2,4-三唑[4,3-a]吡啶

Synthesis of 1,2,4-Triazolo[4,3-a]pyridines by I₂-Catalyzed Oxidative Coupling of 2-Aminopyridines with N-Tosylhydrazones

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