Synthesis of Unsymmetrical Diarylureas via Pd-Catalyzed C-N Cross-Coupling Reactions

被引：70

作者：

Breitler, Simon ^{[1
]}

Oldenhuis, Nathan J. ^{[1
]}

Fors, Brett P. ^{[1
]}

Buchwald, Stephen L. ^{[1
]}

机构：

[1] MIT, Dept Chem, Cambridge, MA 02139 USA

来源：

ORGANIC LETTERS | 2011年 / 13卷 / 12期

基金：

美国国家卫生研究院;

关键词：

UREAS; AMINES; CONVERSION; DISCOVERY; ARYLATION; INHIBITOR; MILD;

D O I：

10.1021/ol201210t

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A facile synthesis of unsymmetrical N,N'-diarylureas is described. The utilization of the Pd-catalyzed arylation of ureas enables the synthesis of an array of diarylureas in good to excellent yields from benzylurea via a one-pot arylation-deprotection protocol, followed by a second arylation.

引用

收藏

页码：3262 / 3265

页数：4

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共 32 条

[1] Regioselective preparation of pyridin-2-yl ureas from 2-chloropyridines catalyzed by Pd(0) [J].

Abad, A ;

Agulló, C ;

Cuñat, AC ;

Vilanova, C .

SYNTHESIS-STUTTGART, 2005, (06) :915-924

[2] Unsymmetrical non-adamantyl N,N-diaryl urea and amide inhibitors of soluble expoxide hydrolase [J].

Anandan, Sampath-Kumar ;

Webb, Heather K. ;

Do, Zung N. ;

Gless, Richard D. .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2009, 19 (15) :4259-4263

[3] Palladium-catalyzed reaction of aryl halides with ureas [J].

Artamkina, GA ;

Sergeev, AG ;

Beletskaya, IP .

TETRAHEDRON LETTERS, 2001, 42 (26) :4381-4384

[4] A scaleable synthesis of BAY 43-9006: A potent Raf kinase inhibitor for the treatment of cancer [J].

Bankston, D ;

Dumas, J ;

Natero, R ;

Riedl, B ;

Monahan, MK ;

Sibley, R .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2002, 6 (06) :777-781

[5] Preparation and reactions of zincated thymine derivatives [J].

Bérillon, L ;

Wagner, R ;

Knochel, P .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (24) :9117-9121

[6] α-pyridylation of chiral amines via urea coupling, lithiation and rearrangement [J].

Clayden, Jonathan ;

Hennecke, Ulrich .

ORGANIC LETTERS, 2008, 10 (16) :3567-3570

[7] Carbonyldiimidazole-Mediated Lossen Rearrangement [J].

Dube, Pascal ;

Nathel, Noah F. Fine ;

Vetelino, Michael ;

Couturier, Michel ;

Aboussafy, Claude Larrivee ;

Pichette, Simon ;

Jorgensen, Matthew L. ;

Hardink, Mark .

ORGANIC LETTERS, 2009, 11 (24) :5622-5625

[8] Water-mediated catalyst preactivation: An efficient protocol for C-N cross-coupling reactions [J].

Fors, Brett P. ;

Krattiger, Philipp ;

Strieter, Eric ;

Buchwald, Stephen L. .

ORGANIC LETTERS, 2008, 10 (16) :3505-3508

[9] An efficient system for the Pd-catalyzed cross-coupling of amides and aryl chlorides [J].

Fors, Brett P. ;

Dooleweerdt, Karin ;

Zeng, Qingle ;

Buchwald, Stephen L. .

TETRAHEDRON, 2009, 65 (33) :6576-6583

[10] Practical synthesis of unsymmetrical ureas from isopropenyl carbamates [J].

Gallou, I ;

Eriksson, M ;

Zeng, XZ ;

Senanayake, C ;

Farina, V .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (17) :6960-6963

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