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

页码：328 / 331

页数：4

共 33 条

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