Synthesis of Quinazolines and Tetrahydroquinazolines: Copper-Catalyzed Tandem Reactions of 2-Bromobenzyl Bromides with Aldehydes and Aqueous Ammonia or Amines

被引：43

作者：

Fan, Xuesen ^{[1
]}

Li, Bin ^{[1
]}

Guo, Shenghai ^{[1
]}

Wang, Yuanyuan ^{[1
]}

Zhang, Xinying ^{[1
]}

机构：

[1] Henan Normal Univ, Key Lab Green Chem Media & React, Sch Chem & Chem Engn,Minist Educ, Collaborat Innovat Ctr Henan Prov Green Mfg Fine, Xinxiang 453007, Peoples R China

来源：

CHEMISTRY-AN ASIAN JOURNAL | 2014年 / 9卷 / 03期

关键词：

2-bromobenzyl bromides; CH functionalization; copper; heterocycles; 1; 2; 3; 4-tetrahydroquinazolines; COUPLING REACTIONS; DERIVATIVES; INHIBITORS; ROUTE;

D O I：

10.1002/asia.201301296

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An efficient synthesis of diversely substituted quinazolines and 1,2,3,4-tetrahydroquinazolines through copper-catalyzed tandem reactions of the readily available 2-bromobenzyl bromides, aldehydes, and aqueous ammonia or amines has been developed. By using ammonia and simple aliphatic amines as the nitrogen source, the present method provides a versatile and practical protocol for the synthesis of quinazolines and 1,2,3,4-tetrahydroquinazolines.

引用

页码：739 / 743

页数：5

共 35 条

[1] The Complementary Competitors: Palladium and Copper in C-N Cross-Coupling Reactions
Beletskaya, Irina P.
Cheprakov, Andrei V.
[J]. ORGANOMETALLICS, 2012, 31 (22) : 7753 - 7808
[2] Dual kinase inhibition in the treatment of breast cancer: Initial experience with the EGFR/ErbB-2 inhibitor lapatinib
Burris, HA
[J]. ONCOLOGIST, 2004, 9 : 10 - 15
[3] Synthesis of quinazolinones and quinazolines
Connolly, DJ
Cusack, D
O'Sullivan, TP
Guiry, PJ
[J]. TETRAHEDRON, 2005, 61 (43) : 10153 - 10202
[4] Copper-mediated coupling reactions and their applications in natural products and designed biomolecules synthesis
Evano, Gwilherm
Blanchard, Nicolas
Toumi, Mathieu
[J]. CHEMICAL REVIEWS, 2008, 108 (08) : 3054 - 3131
[5] Pharmacological rescue of mutant p53 conformation and function
Foster, BA
Coffey, HA
Morin, MJ
Rastinejad, F
[J]. SCIENCE, 1999, 286 (5449) : 2507 - 2510
[6] A SPECIFIC INHIBITOR OF THE EPIDERMAL GROWTH-FACTOR RECEPTOR TYROSINE KINASE
FRY, DW
KRAKER, AJ
MCMICHAEL, A
AMBROSO, LA
NELSON, JM
LEOPOLD, WR
CONNERS, RW
BRIDGES, AJ
[J]. SCIENCE, 1994, 265 (5175) : 1093 - 1095
[7] Discovery of novel small-molecule inhibitors of human epidermal growth factor receptor-2: Combined ligand and target-based approach
Gundla, Rambabu
Kazemi, Roza
Sanam, Ramadevi
Muttineni, Ravikumar
Sarma, Jagarlapudi A. R. P.
Dayam, Raveendra
Neamati, Nouri
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 2008, 51 (12) : 3367 - 3377
[8] Synthesis of Pyrazolo(1,5-c]quinazoline Derivatives through Copper-Catalyzed Tandem Reaction of 5-(2-Bromoaryl)-1H-pyrazoles with Carbonyl Compounds and Aqueous Ammonia
Guo, Shenghai
Wang, Jiliang
Fan, Xuesen
Zhang, Xinying
Guo, Dongqiang
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (07) : 3262 - 3270
[9] CuCl/DABCO/4-HO-TEMPO-Catalyzed Aerobic Oxidative Synthesis of 2-Substituted Quinazolines and 4H-3,1-Benzoxazines
Han, Bing
Yang, Xiu-Long
Wang, Chao
Bai, Yong-Wei
Pan, Tai-Chao
Chen, Xin
Yu, Wei
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (02) : 1136 - 1142
[10] Highly efficient copper-catalyzed cascade synthesis of quinazoline and quinazolinone derivatives
Huang, Cheng
Fu, Yuan
Fu, Hua
Jiang, Yuyang
Zhao, Yufen
[J]. CHEMICAL COMMUNICATIONS, 2008, (47) : 6333 - 6335

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