Oxidative C(sp3)–H functionalization of methyl-azaheteroarenes: a facile route to 1,2,4-triazolo[4,3-a]pyridines

Wei-Zhao Weng; Yin-He Gao; Xue Zhang; Yan-Hua Liu; Ying-Jie Shen; Yan-Ping Zhu; Yuan-Yuan Sun; Qing-Guo Meng; An-Xin Wu

doi:10.1039/C9OB00033J

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Oxidative C(sp³)–H functionalization of methyl-azaheteroarenes: a facile route to 1,2,4-triazolo[4,3-a]pyridines†

Wei-Zhao Weng,‡^a Yin-He Gao,‡^a Xue Zhang,‡^a Yan-Hua Liu,‡^a Ying-Jie Shen,‡^a Yan-Ping Zhu,

*^a Yuan-Yuan Sun,^a Qing-Guo Meng^a and An-Xin Wu

*^b

Author affiliations

* Corresponding authors

^a School of Pharmacy, Key Laboratory of Molecular Pharmacology and Drug Evaluation, Ministry of Education, Collaborative Innovation Center of Advanced Drug Delivery System and Biotech Drugs in Universities of Shandong, Yantai University, Yantai, Shandong, P. R. China
E-mail: chemzyp@foxmail.com

^b Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan, Hubei, P. R. China
E-mail: chwuax@mail.ccnu.edu.cn

Abstract

We herein describe an oxidative [4 + 1] annulation used to prepare 1,2,4-triazolo[4,3-a]pyridines in the presence of I₂–DMSO. This protocol enables synthesis of triazolo[4,3-a]pyridine–quinoline linked diheterocycles via a direct oxidative functionalization of sp³ C–H bonds of 2-methyl-azaheteroarenes. The reaction shows a wide substrate scope and good functional group tolerance.

This article is part of the themed collection: Synthetic methodology in OBC

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Article information

DOI: https://doi.org/10.1039/C9OB00033J
Article type: Communication
Submitted: 06 Jan 2019
Accepted: 23 Jan 2019
First published: 23 Jan 2019

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Org. Biomol. Chem., 2019,17, 2087-2091

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Oxidative C(sp³)–H functionalization of methyl-azaheteroarenes: a facile route to 1,2,4-triazolo[4,3-a]pyridines

W. Weng, Y. Gao, X. Zhang, Y. Liu, Y. Shen, Y. Zhu, Y. Sun, Q. Meng and A. Wu, Org. Biomol. Chem., 2019, 17, 2087 DOI: 10.1039/C9OB00033J

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Organic & Biomolecular Chemistry