Copper(I)-Mediated Cascade Reactions: An Efficient Approach to the Synthesis of Functionalized Benzofuro[3,2-d]pyrimidines

被引：23

作者：

Chao, Bo ^{[1
]}

Lin, Shijun ^{[1
]}

Ma, Qingdong ^{[2
]}

Lu, Dong ^{[1
]}

Hu, Youhong ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, Shanghai 201203, Peoples R China

[2] China Univ Petr, Qingdao 266580, Peoples R China

来源：

ORGANIC LETTERS | 2012年 / 14卷 / 09期

基金：

中国国家自然科学基金;

关键词：

ASYMMETRIC CONJUGATE ADDITION; ONE-POT SYNTHESIS; CATALYZED C-N; FACILE SYNTHESIS; PRIMARY AMIDES; ARYL IODIDES; COPPER; 3-COMPONENT; 1,4-ADDITION; IDENTIFICATION;

D O I：

10.1021/ol300822a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel cascade reaction was developed for the synthesis of diverse members of a series of benzofuro(3,2-d]pyrimidine derivatives. The process utilizes readily prepared 3-chlorochromenones and various commercially available amidines and their analogues as starting materials. This tandem reaction is promoted by using a simple copper(I) reagent and involves a chemoselective Michael addition-heterocyclization-intramolecular cyclization sequence.

引用

页码：2398 / 2401

页数：4

共 45 条

[1] Small molecule inhibitors of E-coli primase, a novel bacterial target [J].

Agarwal, Atul ;

Louise-May, Shirley ;

Thanassi, Jane A. ;

Podos, Steven D. ;

Cheng, Jijun ;

Thoma, Christy ;

Liu, Cuixian ;

Wiles, Jason A. ;

Nelson, David M. ;

Phadke, Avinash S. ;

Bradbury, Barton J. ;

Deshpande, Milind S. ;

Pucci, Michael J. .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2007, 17 (10) :2807-2810

[2] 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

[3] Alumina-Supported Cu(II), A Versatile and Recyclable Catalyst for Regioselective Ring Opening of Aziridines and Epoxides and Subsequent Cyclization to Functionalized 1,4-Benzoxazines and 1,4-Benzodioxanes [J].

Bhadra, Sukalyan ;

Adak, Laksmikanta ;

Samanta, Subhas ;

Islam, A. K. M. Maidul ;

Mukherjee, Manabendra ;

Ranu, Brindaban C. .

JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (24) :8533-8541

[4] Mild and nonracemizing conditions for Ullmann-type diaryl ether formation between aryl iodides and tyrosine derivatives [J].

Cai, Qian ;

He, Gang ;

Ma, Dawei .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (14) :5268-5273

[5]

Chavez F, 2008, Patent, Patent No. [WO2008008359 (C2), 2008008359]

[6] Three-component, one-pot synthesis of novel 2,4-substituted 5-azolylthiopyrimidine library for screening against anti-influenza virus A [J].

Cheng, Gang ;

Li, Shukun ;

Li, Jingya ;

Hu, Youhong .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2008, 18 (03) :1177-1180

[7] Heteroatom-linked indanylpyrazines are corticotropin releasing factor type-1 receptor antagonists [J].

Corbett, Jeffrey W. ;

Rauckhorst, Mark R. ;

Qian, Fang ;

Hoffman, Robert L. ;

Knauer, Christopher S. ;

Fitzgerald, Lawrence W. .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2007, 17 (22) :6250-6256

[8] Identification and hit-to-lead exploration of a novel series of histamine H4 receptor inverse agonists [J].

Cramp, Sue ;

Dyke, Hazel J. ;

Higgs, Christopher ;

Clark, David E. ;

Gill, Matthew ;

Savy, Pascal ;

Jennings, Neil ;

Price, Steve ;

Lockey, Peter M. ;

Norman, Dennis ;

Porres, Soraya ;

Wilson, Francis ;

Jones, Alison ;

Ramsden, Nigel ;

Mangano, Raffaella ;

Leggate, Dan ;

Andersson, Marie ;

Hale, Richard .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2010, 20 (08) :2516-2519

[9] Amino-sugar modular ligands-useful cores for the formation of asymmetric copper 1,4-addition catalysts [J].

De Roma, Antonella ;

Ruffo, Francesco ;

Woodward, Simon .

CHEMICAL COMMUNICATIONS, 2008, (42) :5384-5386

[10] O-arylation versus C-arylation: Copper-catalyzed intramolecular coupling of aryl bromides with 1,3-dicarbonyls [J].

Fang, Yewen ;

Li, Chaozhong .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (17) :6427-6431

← 1 2 3 4 5 →