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
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
收藏
页码:739 / 743
页数:5
相关论文
共 35 条
[1]   The Complementary Competitors: Palladium and Copper in C-N Cross-Coupling Reactions [J].
Beletskaya, Irina P. ;
Cheprakov, Andrei V. .
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 [J].
Burris, HA .
ONCOLOGIST, 2004, 9 :10-15
[3]   Synthesis of quinazolinones and quinazolines [J].
Connolly, DJ ;
Cusack, D ;
O'Sullivan, TP ;
Guiry, PJ .
TETRAHEDRON, 2005, 61 (43) :10153-10202
[4]   Copper-mediated coupling reactions and their applications in natural products and designed biomolecules synthesis [J].
Evano, Gwilherm ;
Blanchard, Nicolas ;
Toumi, Mathieu .
CHEMICAL REVIEWS, 2008, 108 (08) :3054-3131
[5]   Pharmacological rescue of mutant p53 conformation and function [J].
Foster, BA ;
Coffey, HA ;
Morin, MJ ;
Rastinejad, F .
SCIENCE, 1999, 286 (5449) :2507-2510
[6]   A SPECIFIC INHIBITOR OF THE EPIDERMAL GROWTH-FACTOR RECEPTOR TYROSINE KINASE [J].
FRY, DW ;
KRAKER, AJ ;
MCMICHAEL, A ;
AMBROSO, LA ;
NELSON, JM ;
LEOPOLD, WR ;
CONNERS, RW ;
BRIDGES, AJ .
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 [J].
Gundla, Rambabu ;
Kazemi, Roza ;
Sanam, Ramadevi ;
Muttineni, Ravikumar ;
Sarma, Jagarlapudi A. R. P. ;
Dayam, Raveendra ;
Neamati, Nouri .
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 [J].
Guo, Shenghai ;
Wang, Jiliang ;
Fan, Xuesen ;
Zhang, Xinying ;
Guo, Dongqiang .
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 [J].
Han, Bing ;
Yang, Xiu-Long ;
Wang, Chao ;
Bai, Yong-Wei ;
Pan, Tai-Chao ;
Chen, Xin ;
Yu, Wei .
JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (02) :1136-1142
[10]   Highly efficient copper-catalyzed cascade synthesis of quinazoline and quinazolinone derivatives [J].
Huang, Cheng ;
Fu, Yuan ;
Fu, Hua ;
Jiang, Yuyang ;
Zhao, Yufen .
CHEMICAL COMMUNICATIONS, 2008, (47) :6333-6335