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

被引：8

作者：

Jiang, Gan ^{[1
]}

Lin, Yang ^{[1
]}

Cai, Mingzhong ^{[2
]}

Zhao, Hong ^{[1
]}

机构：

[1] Guangdong Pharmaceut Univ, Guangdong Cosmet Engn & Technol Res Ctr, Sch Chem & Chem Engn, Guangzhou 510006, Guangdong, Peoples R China

[2] Jiangxi Normal Univ, Coll Chem & Chem Engn, Nanchang 330022, Jiangxi, Peoples R China

来源：

SYNTHESIS-STUTTGART | 2019年 / 51卷 / 23期

基金：

中国国家自然科学基金;

关键词：

copper catalysis; 1; 2; 3]triazolo[1; 5; a ]pyridines; oxidative cyclization; heterogeneous catalysis; N-N coupling; N BOND-FORMATION; SP(3) C-H; CATALYZED DENITROGENATIVE TRANSANNULATION; CROSS-COUPLING REACTIONS; ONE-POT SYNTHESIS; EFFICIENT SYNTHESIS; COORDINATION-COMPOUNDS; MAGNETIC-PROPERTIES; CRYSTAL-STRUCTURE; MOLECULAR-OXYGEN;

D O I：

10.1055/s-0037-1610726

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：4487 / 4497

页数：11

共 99 条

[1] 3-(2-Pyridyl)-[1,2,3]triazolo[1,5-a]pyridines.: An experimental and theoretical (DFT) study of the ring-chain isomerization [J].