A convenient palladium-catalyzed carbonylative synthesis of quinazolines from 2-aminobenzylamine and aryl bromides

被引:31
作者
Chen, Jianbin [1 ]
Natte, Kishore [1 ]
Neumann, Helfried [1 ]
Wu, Xiao-Feng [1 ]
机构
[1] Univ Rostock, Leibniz Inst Katalyse, D-18059 Rostock, Germany
关键词
STOICHIOMETRIC CARBON-MONOXIDE; ONE-POT SYNTHESIS; O-PHENYL OXIMES; AEROBIC OXIDATION; CASCADE SYNTHESIS; DOMINO REACTIONS; DERIVATIVES; HETEROCYCLES; NUCLEOPHILES; INHIBITORS;
D O I
10.1039/c4ra11303a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A novel and practical strategy towards quinazoline scaffolds synthesis has been achieved. Through palladium-catalyzed carbonylative coupling of 2-aminobenzylamine with aryl bromides, the desired quinazolines were produced in moderate to good yields for the first time. The reactions followed an aminocarbonylation-condensation-oxidation sequence in a one-pot one-step manner. Preliminary investigation showed DMSO serves both as solvent and oxidant in this procedure.
引用
收藏
页码:56502 / 56505
页数:4
相关论文
共 54 条
[1]  
[Anonymous], DOMINO REACTIONS IN
[2]   Palladium-Catalyzed Carbonylation-A Reaction Come of Age [J].
Barnard, Christopher F. J. .
ORGANOMETALLICS, 2008, 27 (21) :5402-5422
[3]   Palladium-Catalyzed Carbonylation Reactions of Aryl Halides and Related Compounds [J].
Brennfuehrer, Anne ;
Neumann, Helfried ;
Beller, Matthias .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (23) :4114-4133
[4]   Pd-Catalyzed Thiocarbonylation with Stoichiometric Carbon Monoxide: Scope and Applications [J].
Burhardt, Mia N. ;
Taaning, Rolf H. ;
Skrydstrup, Troels .
ORGANIC LETTERS, 2013, 15 (04) :948-951
[5]   Base-Controlled Selectivity in the Synthesis of Linear and Angular Fused Quinazolinones by a Palladium-Catalyzed Carbonylation/Nucleophilic Aromatic Substitution Sequence [J].
Chen, Jianbin ;
Natte, Kishore ;
Spannenberg, Anke ;
Neumann, Helfried ;
Langer, Peter ;
Beller, Matthias ;
Wu, Xiao-Feng .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (29) :7579-7583
[6]   Palladium-catalyzed synthesis of isoindoloquinazolinones via dicarbonylation of 1,2-dibromoarenes [J].
Chen, Jianbin ;
Neumann, Helfried ;
Beller, Matthias ;
Wu, Xiao-Feng .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (31) :5835-5838
[7]   Efficient palladium-catalyzed double carbonylation of o-dibromobenzenes: synthesis of thalidomide [J].
Chen, Jianbin ;
Natte, Kishore ;
Spannenberg, Anke ;
Neumann, Helfried ;
Beller, Matthias ;
Wu, Xiao-Feng .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (30) :5578-5581
[8]   Silver triflate-copper(II) acetate cooperative catalysis in a cascade reaction for concise synthesis of 2-carbonyl H-pyrazolo[5,1-a]isoquinolines [J].
Chen, Zhiyuan ;
Gao, Liang ;
Ye, Shengqing ;
Ding, Qiuping ;
Wu, Jie .
CHEMICAL COMMUNICATIONS, 2012, 48 (33) :3975-3977
[9]   Unexpected Copper-Catalyzed Cascade Synthesis of Quinazoline Derivatives [J].
Chen, Zhongyan ;
Chen, Jiuxi ;
Liu, Miaochang ;
Ding, Jinchang ;
Gao, Wenxia ;
Huang, Xiaobo ;
Wu, Huayue .
JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (22) :11342-11348
[10]   Multi-component syntheses of heterocycles by transition-metal catalysis [J].
D'Souza, Daniel M. ;
Mueller, Thomas J. J. .
CHEMICAL SOCIETY REVIEWS, 2007, 36 (07) :1095-1108