Recyclable Heterogeneous Copper(II)-Catalyzed Oxidative Cyclization of 2-Pyridine Ketone Hydrazones Towards [1,2,3]Triazolo[1,5-a]pyridines

Gan Jiang; Yang Lin; Mingzhong Cai; Hong Zhao

doi:10.1055/s-0037-1610726

Synthesis, Table of Contents

Synthesis 2019; 51(23): 4487-4497
DOI: 10.1055/s-0037-1610726

paper

Recyclable Heterogeneous Copper(II)-Catalyzed Oxidative Cyclization of 2-Pyridine Ketone Hydrazones Towards [1,2,3]Triazolo[1,5-a]pyridines

Gan Jiang

^aSchool of Chemistry & Chemical Engineering, Guangdong Cosmetics Engineering & Technology Research Center, Guangdong Pharmaceutical University, Guangzhou 510006, P. R. of China Email: zhaohong1001@sina.com

,

Yang Lin

^aSchool of Chemistry & Chemical Engineering, Guangdong Cosmetics Engineering & Technology Research Center, Guangdong Pharmaceutical University, Guangzhou 510006, P. R. of China Email: zhaohong1001@sina.com

,

Mingzhong Cai ∗

^bCollege of Chemistry & Chemical Engineering, Jiangxi Normal University, Nanchang 330022, P. R. of China Email: mzcai@jxnu.edu.cn

,

Hong Zhao∗

^aSchool of Chemistry & Chemical Engineering, Guangdong Cosmetics Engineering & Technology Research Center, Guangdong Pharmaceutical University, Guangzhou 510006, P. R. of China Email: zhaohong1001@sina.com

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Abstract

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Abstract

The heterogeneous copper(II)-catalyzed oxidative cyclization of 2-pyridine ketone hydrazones was achieved in ethyl acetate at room temperature in the presence of an MCM-41-anchored bidentate 2-aminoethylamino copper(II) catalyst [MCM-41-2N-Cu(OAc)₂], in the presence of air as the oxidant, yielding a wide variety of [1,2,3]triazolo[1,5-a]pyridines in mostly good to high yields. The present method was also applied to the direct one-pot synthesis of [1,2,3]triazolo[1,5-a]pyridines from 2-acylpyridine derivatives and hydrazine monohydrate. Importantly, this supported copper(II) catalyst could be conveniently obtained via a simple procedure from easily available and inexpensive reagents, recovered by filtration of the reaction mixture, and reused at least seven times without a significant loss of catalytic activity.

Key words

copper catalysis - [1,2,3]triazolo[1,5-a]pyridines - oxidative cyclization - heterogeneous catalysis - N–N coupling

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References

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