Copper-Catalyzed Synthesis of Quinazoline Derivatives via Ullmann-Type Coupling and Aerobic Oxidation

被引：135

作者：

Wang, Chen ^{[1
]}

Li, Shangfu ^{[2
]}

Liu, Hongxia ^{[2
]}

Jiang, Yuyang ^{[2
]}

Fu, Hua ^{[1
]}

机构：

[1] Tsinghua Univ, Dept Chem, Minist Educ, Key Lab Bioorgan Phosphorus Chem & Chem Biol, Beijing 100084, Peoples R China

[2] Tsinghua Univ, Key Lab Chem Biol Guangdong Prov, Grad Sch Shenzhen, Shenzhen 518057, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 75卷 / 22期

基金：

中国国家自然科学基金;

关键词：

C-O; EFFICIENT SYNTHESIS; ARYL HALIDES; ORTHO-SUBSTITUENT; CASCADE SYNTHESIS; N-ARYLATION; INHIBITORS; RECEPTOR; LIGAND; AMIDES;

D O I：

10.1021/jo101685d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A simple and efficient copper-catalyzed approach to quinazoline derivatives has been developed, and the protocol uses readily available substituted (2-bromophenyl)methylamines and amides as the starting materials, and the cascade reactions were performed under air via sequential Ullmann-type coupling and aerobic oxidation without addition of any ligand or additive The present method provides a convenient and practical strategy for synthesis of quinazoline derivatives

引用

收藏

页码：7936 / 7938

页数：3

相关论文

共 68 条

[41] Domino Cu-catalyzed C-N coupling/hydroamidation:: A highly efficient synthesis of nitrogen heterocycles [J].

Martin, Ruben ;

Rivero, Marta Rodriguez ;

Buchwald, Stephen L. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (42) :7079-7082

[42] Molecular features of the prazosin molecule required for activation of Transport-P [J].

Mendes da Silva, Joaquim Fernando ;

Walters, Marcus ;

Al-Damluji, Saad ;

Ganellin, C. Robin .

BIOORGANIC & MEDICINAL CHEMISTRY, 2008, 16 (15) :7254-7263

[43] Quinoline, quinazoline and acridone alkaloids [J].

Michael, JP .

NATURAL PRODUCT REPORTS, 2003, 20 (05) :476-493

[44] Synthesis of 2,4-dihydroxyquinazolines using carbon dioxide in the presence of DBU under mild conditions [J].

Mizuno, T ;

Okamoto, N ;

Ito, T ;

Miyata, T .

TETRAHEDRON LETTERS, 2000, 41 (07) :1051-1053

[45] Catalytic C-C, C-N, and C-O Ullmann-Type Coupling Reactions [J].

Monnier, Florian ;

Taillefer, Marc .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (38) :6954-6971

[46] New synthetic technology for the synthesis of aryl ethers: Construction of C-O-D and D-O-E ring model systems of vancomycin [J].

Nicolaou, KC ;

Boddy, CNC ;

Natarajan, S ;

Yue, TY ;

Li, H ;

Brase, S ;

Ramanjulu, JM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (14) :3421-3422

[47] A versatile and efficient ligand for copper-catalyzed formation of C-N, C-o, and P-C bonds: Pyrrolidine-2-phosphonic acid phenyl monoester [J].

Rao, HH ;

Jin, Y ;

Fu, H ;

Jiang, YY ;

Zhao, YF .

CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (13) :3636-3646

[48] Copper-catalyzed arylation of amines using diphenyl pyrrolidine-2-phosphonate as the new ligand [J].

Rao, HH ;

Fu, H ;

Jiang, YY ;

Zhao, YF .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (20) :8107-8109

[49] Highly Efficient Copper-Catalyzed Synthesis of Internal Alkynes via Aerobic Oxidative Arylation of Terminal Alkynes [J].

Rao, Honghua ;

Fu, Hua ;

Jiang, Yuyang ;

Zhao, Yufen .

ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (2-3) :458-462

[50] Tyrosine kinase inhibitors .9. Synthesis and evaluation of fused tricyclic quinazoline analogues as ATP site inhibitors of the tyrosine kinase activity of the epidermal growth factor receptor [J].

Rewcastle, GW ;

Palmer, BD ;

Bridges, AJ ;

Showalter, HDH ;

Li, S ;

Nelson, J ;

McMichael, A ;

Kraker, AJ ;

Fry, DW ;

Denny, WA .

JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (04) :918-928

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