Quinazolinones from o-Aminobenzonitriles by One-Pot Sequential Selective Hydration/Condensation/Acceptorless Dehydrogenation Catalyzed by an Iridium Complex

被引:45
作者
Zhao, Wei [1 ]
Liu, Pengcheng [1 ]
Li, Feng [1 ,2 ]
机构
[1] Nanjing Univ Sci & Technol, Sch Chem Engn, 200 Xiaolingwei St, Nanjing 210094, Jiangsu, Peoples R China
[2] Dalian Univ Technol, State Key Lab Fine Chem, 2 Lingong Rd, Dalian 116024, Peoples R China
基金
中国国家自然科学基金;
关键词
dehydrogenation; heterocycles; homogeneous catalysis; iridium; synthesis design; FUNCTIONAL BIPYRIDONATE LIGAND; N-ALKYLATED AMIDES; ACCEPTORLESS DEHYDROGENATION; PRIMARY ALCOHOLS; NITROGEN-HETEROCYCLES; HYDROGENATION; INHIBITORS; SYSTEM; OXIDATION; NITRILES;
D O I
10.1002/cctc.201501385
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
A new strategy for the direct synthesis of quinazolinones from o-aminobenzonitriles was proposed and accomplished. In the presence of [Cp*IrCl2](2) (Cp*=pentamethylcyclopentadienyl), a variety of desirable products was obtained easily through the one-pot sequential selective hydration/condensation/acceptorless dehydrogenation. This protocol is highly attractive because it uses readily available starting materials, has a high atom efficiency, good to excellent yields, and minimal consumption of chemicals and energy. Notably, this research exhibited new potential for the development of transition-metal-catalyzed one-pot sequential reactions that involve acceptorless dehydrogenation.
引用
收藏
页码:1523 / 1530
页数:8
相关论文
共 79 条
[1]   A novel method for the synthesis of 4(3H)-quinazolinones [J].
Abdel-Jalil, RJ ;
Voelter, W ;
Saeed, M .
TETRAHEDRON LETTERS, 2004, 45 (17) :3475-3476
[2]  
[Anonymous], 2009, ANGEW CHEM-GER EDIT
[3]  
[Anonymous], 2013, Angew. Chem, DOI [DOI 10.1002/ANGE.201300292, 10.1002/ange.201300292]
[4]  
Bailey P.D., 2005, Comprehensive Organic Functional Group Transformations II, V5, P201
[5]   Synthesis, anti-inflammatory evaluation and docking studies of some new fluorinated fused quinazolines [J].
Balakumar, C. ;
Lamba, P. ;
Kishore, D. Pran ;
Narayana, B. Lakshmi ;
Rao, K. Venkat ;
Rajwinder, K. ;
Rao, A. Raghuram ;
Shireesha, B. ;
Narsaiah, B. .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2010, 45 (11) :4904-4913
[6]   Synthesis and in vitro antitumor activity of 4(3H)-quinazolinone derivatives with dithiocarbamate side chains [J].
Cao, SL ;
Feng, YP ;
Jiang, YY ;
Liu, SY ;
Ding, GY ;
Li, RT .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2005, 15 (07) :1915-1917
[7]   A Single Nickel Catalyst for the Acceptorless Dehydrogenation of Alcohols and Hydrogenation of Carbonyl Compounds [J].
Chakraborty, Sumit ;
Piszel, Paige E. ;
Brennessel, William W. ;
Jones, William D. .
ORGANOMETALLICS, 2015, 34 (21) :5203-5206
[8]   Well-Defined Iron Catalysts for the Acceptor less Reversible Dehydrogenation-Hydrogenation of Alcohols and Ketones [J].
Chakraborty, Sumit ;
Lagaditis, Paraskevi O. ;
Foerster, Moritz ;
Bielinski, Elizabeth A. ;
Hazari, Nilay ;
Holthausen, Max C. ;
Jones, William D. ;
Schneider, Sven .
ACS CATALYSIS, 2014, 4 (11) :3994-4003
[9]   A Molecular Iron Catalyst for the Acceptorless Dehydrogenation and Hydrogenation of N-Heterocycles [J].
Chakraborty, Sumit ;
Brennessel, William W. ;
Jones, William D. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (24) :8564-8567
[10]   Palladium-Catalyzed Carbonylative Reactions of 1-Bromo-2-fluorobenzenes with Various Nucleophiles: Effective Combination of Carbonylation and Nucleophilic Substitution [J].
Chen, Jianbin ;
Natte, Kishore ;
Neumann, Helfried ;
Wu, Xiao-Feng .
CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (49) :16107-16110