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.
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收藏
页码：1635 / 1645
页数：11
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