Copper-Catalyzed Cascade Amination Route to N-Aryl Benzimidazoquinazolinones

被引:27
作者
Banerjee, Arpan [1 ]
Subramanian, Parthasarathi [1 ]
Kaliappan, Krishna P. [1 ]
机构
[1] Indian Inst Technol, Dept Chem, Bombay 400076, Maharashtra, India
关键词
C-H AMINATION; ONE-POT; BOND FORMATION; KINASE INHIBITORS; DERIVATIVES; ACTIVATION; EFFICIENT; HETEROARYL; AMIDATION; CLEAVAGE;
D O I
10.1021/acs.joc.6b01287
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient one-pot Cu-catalyzed C-H functionalization/two-fold C-N bond formation protocol for the syntheses of N-aryl benzimidazoquinazolinones is being reported. This strategy involves a Cu-catalyzed C-N bond coupling reaction between N-anilinoquinazolinones and aryl/heteroaryl halides followed by acetate ligand-assisted intramolecular C-H amination.(1a) This reaction is high-yielding and straightforward for the synthesis of anti-cancer drug analogues of benzimidazoquinazolinones.
引用
收藏
页码:10424 / 10432
页数:9
相关论文
共 75 条
[21]   Palladium-catalyzed amination of aryl halides: Mechanism and rational catalyst design [J].
Hartwig, JF .
SYNLETT, 1997, (04) :329-+
[22]   Evolution of a Fourth Generation Catalyst for the Amination and Thioetherification of Aryl Halides [J].
Hartwig, John F. .
ACCOUNTS OF CHEMICAL RESEARCH, 2008, 41 (11) :1534-1544
[23]   Recent advances in 4(3H)-quinazolinone syntheses [J].
He, Lin ;
Li, Haoquan ;
Chen, Jianbin ;
Wu, Xiao-Feng .
RSC ADVANCES, 2014, 4 (24) :12065-12077
[24]   Design and structure-activity relationship of a new class of potent VEGF receptor tyrosine kinase inhibitors [J].
Hennequin, LF ;
Thomas, AP ;
Johnstone, C ;
Stokes, ESE ;
Plé, PA ;
Lohmann, JJM ;
Ogilvie, DJ ;
Dukes, M ;
Wedge, SR ;
Curwen, JO ;
Kendrew, J ;
Lambert-van der Brempt, C .
JOURNAL OF MEDICINAL CHEMISTRY, 1999, 42 (26) :5369-5389
[25]  
Heravi MM, 2011, B CHEM SOC ETHIOPIA, V25, P305
[26]   The combinatorial synthesis of bicyclic privileged structures or privileged substructures [J].
Horton, DA ;
Bourne, GT ;
Smythe, ML .
CHEMICAL REVIEWS, 2003, 103 (03) :893-930
[27]   Palladium-catalyzed C-H activation/intramolecular amination reaction: A new route to 3-aryl/alkylindazoles [J].
Inamoto, Kiyofumi ;
Saito, Tadataka ;
Katsuno, Mika ;
Sakamoto, Takao ;
Hiroya, Kou .
ORGANIC LETTERS, 2007, 9 (15) :2931-2934
[28]   Transition-Metal-Catalyzed Selective Cyclization Strategy to 2-Substituted Benzofurans and Indoles en Route to the Oxa Analogues of Isocryptolepine [J].
Indu, Satrajit ;
Subramanian, Parthasarathi ;
Kaliappan, Krishna P. .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (32) :7193-7202
[29]   Oxidative Pd(II)-Catalyzed C-H Bond Amination to Carbazole at Ambient Temperature [J].
Jordan-Hore, James A. ;
Johansson, Carin C. C. ;
Gulias, Moises ;
Beck, Elizabeth M. ;
Gaunt, Matthew J. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (48) :16184-+
[30]  
Jouvin K., 2013, COPPER MEDIATED CROS, P187