Hofmann Rearrangement of Carboxamides Mediated by N-Bromoacetamide

被引：15
|
作者：
Jevtic, Ivana I. [1 ]
Dosen-Micovic, Ljiljana [1 ]
Ivanovic, Evica R. [2 ]
Ivanovic, Milovan D. [1 ]
机构：
[1] Univ Belgrade, Fac Chem, Studentski Trg 12-16, Belgrade 11000, Serbia
[2] Univ Belgrade, Fac Agr, Nemanjina 6, Belgrade 11080, Serbia
来源：
SYNTHESIS-STUTTGART | 2016年 / 48卷 / 10期
关键词：
Hofmann rearrangement; amides; stereoselectivity; cyclization; heterocycles; PRIMARY AMIDES; TERMINAL OXIDANT; IN-SITU; PHARMACOLOGY; DISCOVERY; CYANATE; OXONE; ACID;
D O I：
10.1055/s-0035-1561405
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient, one-pot procedure for the Hofmann rearrangement of aromatic and aliphatic amides has been developed. Methyl and benzyl carbamates are produced with N-bromoacetamide in the presence of lithium hydroxide or lithium methoxide, in high yields. -Phenylamino amides gave five-membered cyclic ureas stereospecifically. Side products of aryl or benzyl bromination were minimized. This procedure offers an easy access to various protected amines or diamines, which represent important synthetic precursors.
引用
收藏
页码：1550 / 1560
页数：11
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