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

页码：3482 / 3485

页数：4

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