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Paper | Regular issue | Vol 104, No. 2, 2022, pp.310-325
Published online, 18th November, 2021
DOI: 10.3987/COM-21-14576
Metal-Free C3-H Hydrazination of Imidazo[1,2-a]pyridine with Azodiformates in Water at Room Temperature

Huijie Qiao,* Liting Yang, Wuxuan Sun, Ya Chen, Jialin Wang, Yunwei Wang, and Haobo Dong

*School of Materials and Chemical Engineering, Zhongyuan University of Technology, Henan 450007, P. R. China

Abstract

An efficient synthesis of imidazo[1,2-a]pyridine-hydrazines was accomplished by making imidazo[1,2-a]pyridine substrates and azodiformates react in water phase. This reaction features mild and green conditions (proceeding without transition-metals and phase transfer catalyst in water under air at room temperature) as well as good tolerance of substrates. Note that electron-donating groups on the imidazo[1,2-a]pyridine substrates are benefit for this reaction, affording target products in excellent yields. Besides, this aqueous phase reaction could also tolerate the solid azodiformates.