Copper catalyzed oxidative coupling of amines with formamides: a new approach for the synthesis of unsymmetrical urea derivatives

被引：46

作者：

Kumar, G. Sathish ^{[1
]}

Kumar, R. Arun ^{[1
]}

Kumar, P. Santhosh ^{[1
]}

Reddy, N. Veera ^{[1
]}

Kumar, K. Vijaya ^{[1
]}

Kantam, M. Lakshmi ^{[1
]}

Prabhakar, S. ^{[2
]}

Reddy, K. Rajender ^{[1
]}

机构：

[1] Indian Inst Chem Technol CSIR IICT, Inorgan & Phys Chem Div, Hyderabad 500607, Andhra Pradesh, India

[2] Indian Inst Chem Technol, Natl Ctr Mass Spectrometry, Hyderabad 500607, Andhra Pradesh, India

来源：

CHEMICAL COMMUNICATIONS | 2013年 / 49卷 / 59期

关键词：

C-H BONDS; PROTEASE INHIBITORS; DIRECT AMIDATION; SINGLE-ELECTRON; CARBON-DIOXIDE; ACTIVATION; CYANATION; ALDEHYDES; PHOSGENE; ALCOHOLS;

D O I：

10.1039/c3cc42381f

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Direct access to unsymmetrical urea derivatives via copper catalysed C-H/N-H coupling of formamides with amines has been developed at room temperature. This protocol is also applied to the synthesis of chiral urea derivatives.

引用

页码：6686 / 6688

页数：3

共 68 条

[1]

Batra Sanjay, 2006, Anti-Infective Agents in Medicinal Chemistry, V5, P135, DOI 10.2174/187152106776359048

[2] Selected syntheses of ureas through phosgene substitutes [J].

Bigi, F ;

Maggi, R ;

Sartori, G .

GREEN CHEMISTRY, 2000, 2 (04) :140-148

[3] A novel synthesis of isocyanates and ureas via β-elimination of haloform [J].

Braverman, S ;

Cherkinsky, M ;

Kedrova, L ;

Reiselman, A .

TETRAHEDRON LETTERS, 1999, 40 (16) :3235-3238

[4] Synthesis and cytotoxic evaluation of substituted urea derivatives as inhibitors of human-leukemia K562 cells [J].

Cao, Ping ;

Huang, Xian-Feng ;

Ding, Hui ;

Ge, Hui-Ming ;

Li, Huan-Qiu ;

Ruan, Ban-Feng ;

Zhu, Hai-Liang .

CHEMISTRY & BIODIVERSITY, 2007, 4 (05) :881-886

[5] Pyrrolidine-ureas as bifunctional organocatalysts for asymmetric Michael addition of ketone to nitroalkenes: unexpected hydrogen bonding effect [J].

Cao, Xiao-Yu ;

Zheng, Jun-Cheng ;

Li, Yu-Xue ;

Shu, Zhen-Cao ;

Sun, Xiu-Li ;

Wang, Bi-Qin ;

Tang, Yong .

TETRAHEDRON, 2010, 66 (51) :9703-9707

[6] Pd(II)-Catalyzed Enantioselective C-H Activation/C-O Bond Formation: Synthesis of Chiral Benzofuranones [J].

Cheng, Xiu-Fen ;

Li, Yan ;

Su, Yi-Ming ;

Yin, Feng ;

Wang, Jian-Yong ;

Sheng, Jie ;

Vora, Harit U. ;

Wang, Xi-Sheng ;

Yu, Jin-Quan .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (04) :1236-1239

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

Clayden, Jonathan ;

Hennecke, Ulrich .

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

[8] Substituted diarylmethylamines by stereospecific intramolecular electrophilic arylation of lithiated ureas [J].

Clayden, Jonathan ;

Dufour, Jeremy ;

Grainger, Damian M. ;

Helliwell, Madeleine .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (24) :7488-+

[9] Three-dimensional quantitative structure-activity relationship study on cyclic urea derivatives as HIV-1 protease inhibitors: Application of comparative molecular field analysis [J].

Debnath, AK .

JOURNAL OF MEDICINAL CHEMISTRY, 1999, 42 (02) :249-259

[10] Transition metal-catalyzed oxidative carbonylation of amines to ureas [J].

Diaz, Delmy J. ;

Darko, Ampofo K. ;

McElwee-White, Lisa .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (27) :4453-4465

← 1 2 3 4 5 6 7 →