Facile synthesis of 3,5-diaryl-1,2,4-triazoles via copper-catalyzed domino nucleophilic substitution/oxidative cyclization using amidines or imidates as substrates

被引：32

作者：

Sudheendran, Kavitha ^{[1
]}

Schmidt, Dietmar ^{[1
]}

Frey, Wolfgang ^{[2
]}

Conrad, Juergen ^{[1
]}

Beifuss, Uwe ^{[1
]}

机构：

[1] Univ Hohenheim, Inst Chem, D-70599 Stuttgart, Germany

[2] Univ Stuttgart, Inst Organ Chem, D-70569 Stuttgart, Germany

来源：

TETRAHEDRON | 2014年 / 70卷 / 08期

关键词：

Amidine; Imidate; Catalysis; Copper; 1,2,4-Triazole; COORDINATION CHEMISTRY; COUPLING REACTIONS; ANTIFUNGAL AGENTS; TRIAZOLE; 1,2,4-TRIAZOLES; DERIVATIVES; PREGNANCY; NITRILES; ARYL; COMBINATION;

D O I：

10.1016/j.tet.2014.01.019

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Two methods for the synthesis of 3,5-diaryl-1,2,4-triazoles, both domino reactions, are reported. The first procedure, the Cu(OTf)(2)-catalyzed reaction between two amidines using NaHCO3 as a base, 1,10-phenanthroline as an additive and K-3[Fe(CN)(6)]/atmospheric oxygen as the oxidant, delivers 3,5-diaryl-1,2,4-triazoles with yields up to 68%. The second procedure for the synthesis of 3,5-diaryl-1,2,4-triazoles with yields up to 64% rests on the Cu(OTf)(2)-catalyzed reaction between two imidates and ammonium carbonate. This method features the formation of three bonds in a single synthetic step. (C) 2014 Elsevier Ltd. All rights reserved.

引用

页码：1635 / 1645

页数：11

共 40 条

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