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
[1]   Transition-Metal-Catalyzed Direct Arylation of (Hetero)Arenes by C-H Bond Cleavage [J].
Ackermann, Lutz ;
Vicente, Ruben ;
Kapdi, Anant R. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (52) :9792-9826
[2]   Cu-catalyzed Goldberg and Ullmann reactions of aryl halides using chelating N- and O-based ligands [J].
Altman, Ryan A. ;
Buchwald, Stephen L. .
NATURE PROTOCOLS, 2007, 2 (10) :2474-2479
[3]   Systematic review: Agranulocytosis induced by nonchemotherapy drugs [J].
Andersohn, Frank ;
Konzen, Christine ;
Garbe, Edeltraut .
ANNALS OF INTERNAL MEDICINE, 2007, 146 (09) :657-665
[4]   Monodentate phosphines provide highly active catalysts for Pd-catalyzed C-N bond-forming reactions of heteroaromatic halides/amines and (H)N-heterocycles [J].
Anderson, Kevin W. ;
Tundel, Rachel E. ;
Ikawa, Takashi ;
Altman, Ryan A. ;
Buchwald, Stephen L. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (39) :6523-6527
[5]   THE THERMAL REARRANGEMENT OF 2-ARYL-1-CYANOINDAZOL-3-ONES [J].
BIRD, CW ;
KAPILI, M .
TETRAHEDRON, 1987, 43 (20) :4621-4624
[6]   Preparation of Fused Tetracyclic Quinazolinones by Combinations of Aza-Wittig Methodologies and CuI-Catalysed Heteroarylation Processes [J].
Bleda, Juan Antonio ;
Fresneda, Pilar M. ;
Orenes, Raul ;
Molina, Pedro .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (15) :2490-2504
[7]   Luotonin A. A naturally occurring human DNA topoisomerase I poison [J].
Cagir, A ;
Jones, SH ;
Gao, R ;
Eisenhauer, BM ;
Hecht, SM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (45) :13628-13629
[8]   Microwave-mediated heterocyclization to benzimidazo[2,1-b]quinazolin-12(5H)-ones [J].
Carpenter, Richard D. ;
Lam, Kit S. ;
Kurth, Mark J. .
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (01) :284-287
[9]   Silica gel/FeCl3:: An efficient and recyclable heterogenous catalyst for one step synthesis of 4(3H)-quinazolinones under solvent free conditions [J].
Chari, M. Adharvana ;
Shobha, D. ;
Mukkanti, K. .
CATALYSIS COMMUNICATIONS, 2006, 7 (10) :787-790
[10]   Copper-Catalyzed Aerobic Oxidative Synthesis of 5-Substituted Imidazo/Benzimidazoquinazolinones through Intramolecular C-H Amination [J].
Chen, Lujun ;
Li, Chao ;
Bi, Xin ;
Liu, Hongxia ;
Qiao, Renzhong .
ADVANCED SYNTHESIS & CATALYSIS, 2012, 354 (09) :1773-1779