Copper-Catalyzed Aerobic [3+2]-Annulation of N-Alkenyl Amidines

被引：166

作者：

Wang, Yi-Feng ^{[1
]}

Zhu, Xu ^{[1
]}

Chiba, Shunsuke ^{[1
]}

机构：

[1] Nanyang Technol Univ, Div Chem & Biol Chem, Sch Phys & Math Sci, Singapore 637371, Singapore

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2012年 / 134卷 / 08期

关键词：

CU(I)-CATALYZED REGIOSELECTIVE DIAMINATION; PROMOTED INTRAMOLECULAR DIAMINATION; ELECTROPHILIC DIAMINATION; BOND FORMATION; CONJUGATED DIENES; MECHANISTIC PATHWAYS; AZIRIDINATION; OXIDATION; UREAS; 1,2-DIAMINATION;

D O I：

10.1021/ja2120629

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A method for the synthesis of bi- and tricyclic amidines has been developed through copper-catalyzed aerobic [3+2]-annulation reaction of N-alkenyl amidines. These cyclic amidines could be converted into mono-benzyl-protected vicinal diamines by the reduction with aluminum hydride.

引用

页码：3679 / 3682

页数：4

共 79 条

[1] Pd(II)-catalyzed intermolecular 1,2-diamination of conjugated dienes [J].

Bar, GLJ ;

Lloyd-Jones, GC ;

Booker-Milburn, KI .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (20) :7308-7309

[2] Ritter-type reactions of N-chlorosaccharin:: A method for the electrophilic diamination of alkenes [J].

Booker-Milburn, KI ;

Guly, DJ ;

Cox, B ;

Procopiou, PA .

ORGANIC LETTERS, 2003, 5 (18) :3313-3315

[3] Mechanistic studies of copper-catalyzed alkene aziridination [J].

Brandt, P ;

Södergren, MJ ;

Andersson, PG ;

Norrby, PO .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (33) :8013-8020

[4] C-H functionalization/C-N bond formation: Copper-catalyzed synthesis of benzimidazoles from amidines [J].

Brasche, Gordon ;

Buchwald, Stephen L. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (10) :1932-1934

[5] SELECTIVE REDUCTIONS .X. REACTION OF ALUMINUM HYDRIDE WITH SELECTED ORGANIC COMPOUNDS CONTAINING REPRESENTATIVE FUNCTIONAL GROUPS . COMPARISON OF REDUCING CHARACTERISTICS OF LITHIUM ALUMINUM HYDRIDE AND ITS DERIVATIVES [J].

BROWN, HC ;

YOON, NM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1966, 88 (07) :1464-&

[6]

Cardona F, 2009, NAT CHEM, V1, P269, DOI [10.1038/nchem.256, 10.1038/NCHEM.256]

[7] Analysis of the reactions used for the preparation of drug candidate molecules [J].

Carey, John S. ;

Laffan, David ;

Thomson, Colin ;

Williams, Mike T. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (12) :2337-2347

[8] Preparation and Utility of Trihaloethyl Imidates: Useful Reagents for the Synthesis of Amidines [J].

Caron, Stephane ;

Wei, Lulin ;

Douville, Jasmin ;

Ghosh, Arun .

JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (03) :945-947

[9] Cu(II)-catalyzed functionalizations of aryl C-H bonds using O2 as an oxidant [J].

Chen, Xiao ;

Hao, Xue-Shi ;

Goodhue, Charles E. ;

Yu, Jin-Quan .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (21) :6790-6791

[10] Copper-Catalyzed Synthesis of Azaspirocyclohexadienones from α-Azido-N-arylamides under an Oxygen Atmosphere [J].

Chiba, Shunsuke ;

Zhang, Line ;

Lee, Jian-Yuan .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (21) :7266-+

← 1 2 3 4 5 6 7 8 →