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

共 59 条

[1] Cascade Palladium- and Copper-Catalysed Aromatic Heterocycle Synthesis: The Emergence of General Precursors [J].

Ball, Catherine J. ;

Willis, Michael C. .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (03) :425-441

[2] Palladium-catalyzed cross-coupling between vinyl halides and tert-butyl carbazate:: First general synthesis of the unusual N-Boc-N-alkenylhydrazines [J].

Barluenga, Jose ;

Moriel, Patricia ;

Aznar, Fernando ;

Valdes, Carlos .

ORGANIC LETTERS, 2007, 9 (02) :275-278

[3]

Blumenkopf A. T., 2001, [No title captured], Patent No. [WO 2001040215 A1 20010607, 2001040215]

[4]

Bullock W. H., 2002, [No title captured], Patent No. [WO 2002020526 A2 20020314, 2002020526]

[5] Diversity-Oriented Synthesis of Hydrazine-Derived Compounds from Amino Isocyanates Generated In Situ [J].

Clavette, Christian ;

Rocan, Jean-Francois Vincent ;

Beauchemin, Andre M. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (48) :12705-12708

[6] A Tunable Route for the Synthesis of Azomethine Imines and β-Aminocarbonyl Compounds from Alkenes [J].

Clavette, Christian ;

Gan, Wei ;

Bongers, Amanda ;

Marldewicz, Thomas ;

Toderian, Amy B. ;

Gorelsky, Serge I. ;

Beauchemin, Andre M. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (39) :16111-16114

[7] Methyl Hydrazinocarboxylate as a Practical Alternative to Hydrazine in the Wolff-Kishner Reaction [J].

Cranwell, Philippa B. ;

Russell, Andrew T. ;

Smith, Christopher D. .

SYNLETT, 2016, 27 (01) :131-135

[8] On the Versatility of Urethane/Urea Bonds: Reversibility, Blocked Isocyanate, and Non-isocyanate Polyurethane [J].

Delebecq, Etienne ;

Pascault, Jean-Pierre ;

Boutevin, Bernard ;

Ganachaud, Francois .

CHEMICAL REVIEWS, 2013, 113 (01) :80-118

[9] Divergent Reactivity of N-Isocyanates with Primary and Secondary Amines: Access to Pyridazinones and Triazinones [J].

Derasp, Joshua S. ;

Vincent-Rocan, Jean-Francois ;

Beauchemin, Andre M. .

ORGANIC LETTERS, 2016, 18 (04) :658-661

[10] Synthesis of 2-Aminobenzothiazole via Copper(I)-Catalyzed Tandem Reaction of 2-Iodobenzenamine with Isothiocyanate [J].

Ding, Qiuping ;

He, Xiaodan ;

Wu, Jie .

JOURNAL OF COMBINATORIAL CHEMISTRY, 2009, 11 (04) :587-591

← 1 2 3 4 5 6 →