Regioselective Synthesis of Benzimidazolones via Cascade C-N Coupling of Monosubstituted Ureas

被引：25
作者：
Ernst, Johannes B. [1 ]
Tay, Nicholas E. S. [1 ]
Jui, Nathan T. [1 ]
Buchwald, Stephen L. [1 ]
机构：
[1] MIT, Dept Chem, Cambridge, MA 02139 USA
来源：
ORGANIC LETTERS | 2014年 / 16卷 / 14期
基金：
美国国家卫生研究院;
关键词：
CATALYZED INTRAMOLECULAR CYCLIZATION; SUBSTITUTED 1,3-DIHYDROBENZIMIDAZOL-2-ONES; INHIBITORS; SERIES; HETEROCYCLES; DERIVATIVES; ANTAGONIST; AMINATION; DISCOVERY; ARYLATION;
D O I：
10.1021/ol501531q
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A direct method for the regioselective construction of benzimidazolones is reported wherein a single palladium catalyst is employed to couple monosubstituted urea substrates with differentially substituted 1,2-dihaloaromatic systems. In this method, the catalyst is able to promote a cascade of two discrete chemoselective C-N bond-forming processes that allows the highly selective and predictable formation of complex heterocycles from simple, readily available starting materials.
引用
收藏
页码：3844 / 3846
页数：3
相关论文
共 39 条
[1]   A domino copper-catalyzed C-N and C-O cross-coupling for the conversion of primary amides into benzoxazoles [J].
Altenhoff, G ;
Glorius, F .
ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (13-15) :1661-1664
[2]   Palladium-catalyzed reaction of aryl halides with ureas [J].
Artamkina, GA ;
Sergeev, AG ;
Beletskaya, IP .
TETRAHEDRON LETTERS, 2001, 42 (26) :4381-4384
[3]   Copper-catalyzed intramolecular N-arylation of ureas in water:: a novel entry to benzoimidazolones [J].
Barbero, Nekane ;
Carril, Monica ;
SanMartin, Raul ;
Dominguez, Esther .
TETRAHEDRON, 2008, 64 (30-31) :7283-7288
[4]   Synthesis of 2-substituted-benzothiazoles by palladium-catalyzed intramolecular cyclization of o-bromophenylthioureas and o-bromophenylthioamides [J].
Benedí, C ;
Bravo, F ;
Uriz, P ;
Fernández, E ;
Claver, C ;
Castillón, S .
TETRAHEDRON LETTERS, 2003, 44 (32) :6073-6077
[5]   Potassium Hydroxide/Dimethyl Sulfoxide Promoted Intramolecular Cyclization for the Synthesis of Benzimidazol-2-ones [J].
Beyer, Astrid ;
Reucher, Christine M. M. ;
Bolm, Carsten .
ORGANIC LETTERS, 2011, 13 (11) :2876-2879
[6]   Synthesis of Unsymmetrical Diarylureas via Pd-Catalyzed C-N Cross-Coupling Reactions [J].
Breitler, Simon ;
Oldenhuis, Nathan J. ;
Fors, Brett P. ;
Buchwald, Stephen L. .
ORGANIC LETTERS, 2011, 13 (12) :3262-3265
[7]   Design and preparation of new palladium precatalysts for C-C and C-N cross-coupling reactions [J].
Bruno, Nicholas C. ;
Tudge, Matthew T. ;
Buchwald, Stephen L. .
CHEMICAL SCIENCE, 2013, 4 (03) :916-920
[8]   Rapid and Efficient Trifluoromethylation of Aromatic and Heteroaromatic Compounds Using Potassium Trifluoroacetate Enabled by a Flow System [J].
Chen, Mao ;
Buchwald, Stephen L. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (44) :11628-11631
[9]   Continuous-Flow Synthesis of 1-Substituted Benzotriazoles from Chloronitrobenzenes and Amines in a CN Bond Formation/Hydrogenation/Diazotization/Cyclization Sequence [J].
Chen, Mao ;
Buchwald, Stephen L. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (15) :4247-4250
[10]   Mild and Rapid Pd-Catalyzed Cross-Coupling with Hydrazine in Continuous Flow: Application to the Synthesis of Functionalized Heterocycles [J].
DeAngelis, Andrew ;
Wang, Dong-Hui ;
Buchwald, Stephen L. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (12) :3434-3437
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