Synthesis of 1,2,4-Triazolines: Base-Catalyzed Hydrazination/Cyclization Cascade of α-Isocyano Esters and Amides

被引：71
|
作者：
Monge, David [1 ]
Jensen, Kim L. [1 ]
Marin, Irene [1 ]
Jorgensen, Karl Anker [1 ]
机构：
[1] Aarhus Univ, Ctr Catalysis, DK-8000 Aarhus C, Denmark
来源：
ORGANIC LETTERS | 2011年 / 13卷 / 02期
关键词：
BOND-FORMING REACTIONS; DIELS-ALDER REACTION; DIETHYL AZODICARBOXYLATE; MULTICOMPONENT REACTION; MITSUNOBU REACTION; DERIVATIVES; OXAZOLES; 4-PHENYL-3H-1,2,4-TRIAZOLE-3,5(4H)-DIONE; REACTIVITY; STRATEGY;
D O I：
10.1021/ol102812c
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A convenient, efficient synthesis of 1,2,4-triazolines from alpha-isocyano esters/amides and azodicarboxylates is presented. The developed reaction cascade is based on a base-catalyzed hydrazination-type reaction followed by a subsequent cyclization providing the triazolines in good to excellent yields (75-99%). Phosphine-catalyzed and preliminary asymmetric phase-transfer catalysis approaches have also been investigated.
引用
收藏
页码：328 / 331
页数：4
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