One-pot synthesis of [1,2,4]Triazolo[1,5-a]pyridines from azines and benzylidenemalononitriles via copper-catalyzed tandem cyclization

被引：15

作者：

Lv, Jianguang ^{[1
]}

He, Zhiqing ^{[1
]}

Zhang, Jianmin ^{[1
,2
]}

Guo, Yuwei ^{[1
]}

Han, Ziwei ^{[1
]}

Bao, Xinhua ^{[1
]}

机构：

[1] Shanghai Univ, Innovat Drug Res Ctr, Dept Chem, Shanghai 200444, Peoples R China

[2] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Organofluorine Chem, Shanghai 200032, Peoples R China

来源：

TETRAHEDRON | 2018年 / 74卷 / 29期

关键词：

1,2,4)triazolo[1,5-a]pyridine; Copper-catalyzed; Demethylation; Fluorescence; Tandem cyclization; SOLVENT-FREE CONDITIONS; ONE-STEP SYNTHESIS; N BOND FORMATION; RING-SYSTEM; MICROWAVE IRRADIATION; OXIDATIVE CYCLIZATION; KINASE INHIBITORS; HYDROGEN-TRANSFER; DERIVATIVES; 1,2,4-TRIAZOLES;

D O I：

10.1016/j.tet.2018.06.002

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A simple and efficient copper-catalyzed tandem radical cyclization reaction has been discovered for the synthesis of triaryl [1,2,4]triazolo[1,5-a]pyridines from easily accessible azines and benzylidenmalononitriles. The new transformation involves multiple C-H/C-C bonds cleavage and C-C/C-N bonds formation, with extrusion of gaseous hydrogen and methane. A wide variety of substrates with different functional groups could be converted into the corresponding products in good yields. The fused heterocycles have strong blue fluorescence with large Strokes shifts and high quantum yields. (C) 2018 Elsevier Ltd. All rights reserved.

引用

页码：3996 / 4004

页数：9

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