Copper-Catalyzed Cascade Substitution/Cyclization of N-Isocyanates: A Synthesis of 1-Aminobenzimidazolones

被引：20
|
作者：
An, Jing [1 ]
Alper, Howard [1 ]
Beauchemin, Andre M. [1 ]
机构：
[1] Univ Ottawa, Dept Chem & Biomol Sci, Ctr Catalysis Res & Innovat, 10 Marie Curie, Ottawa, ON K1N 6N5, Canada
来源：
ORGANIC LETTERS | 2016年 / 18卷 / 14期
基金：
加拿大自然科学与工程研究理事会;
关键词：
ONE-POT SYNTHESIS; AZOMETHINE IMINES; REACTIVITY; ARYLATION; AMINO; DERIVATIVES; HYDRAZIDES; BONDS; PART;
D O I：
10.1021/acs.orglett.6b01686
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A copper-catalyzed cascade reaction of in situ generated nitrogen-substituted isocyanates (N-isocyanates) and 2-iodoanilines has been developed. The cascade relies on the base-catalyzed substitution of masked N-isocyanates, followed by Cu(I)-catalyzed coupling to afford a variety of 1-amino-benzimidazolones in moderate to excellent yields. This is the first example of a transition-metal-catalyzed cascade reaction involving N-isocyanate intermediates.
引用
收藏
页码：3482 / 3485
页数：4
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