Copper-catalyzed tandem oxidative synthesis of quinazolinones from 2-aminobenzonitriles and benzyl alcohols

被引：47
作者：
Hu, Yongke [1 ,2 ]
Li, Shaozhong [1 ]
Li, Huaju [1 ]
Li, Yanxing [1 ]
Li, Jin [1 ]
Duanmu, Chuansong [1 ]
Li, Bindong [2 ]
机构：
[1] Huaiyin Inst Technol, Sch Chem Engn, Natl & Local Joint Engn Res Ctr Mineral Salt Deep, Huaian 223003, Peoples R China
[2] Nanjing Univ Sci & Technol, Sch Chem Engn, Nanjing 210094, Jiangsu, Peoples R China
来源：
ORGANIC CHEMISTRY FRONTIERS | 2019年 / 6卷 / 15期
关键词：
ONE-POT SYNTHESIS; MOLECULAR-OXYGEN; AEROBIC OXIDATION; IRON NITRATE/TEMPO; SECONDARY ALCOHOLS; O-AMINOBENZAMIDES; CASCADE SYNTHESIS; HYDRATION; NITRILES; EFFICIENT;
D O I：
10.1039/c9qo00657e
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient and practical copper-catalyzed process for the synthesis of substituted quinazolinones from simple and readily available 2-aminobenzonitriles and benzyl alcohols is described. This method features high functional-group tolerance and could afford a variety of desirable products in good to excellent yields with air as the sole oxidant. Moreover, a possible reaction mechanism is proposed according to the control experiments and reported literature.
引用
收藏
页码：2744 / 2748
页数：5
相关论文
共 58 条
[1]   Synthesis of some new 4(3H)-quinazolinone-2-carboxaldehyde thiosemicarbazones and their metal complexes and a study on their anticonvulsant, analgesic, cytotoxic and antimicrobial activities - Part-1 [J].
Aly, Mohsen M. ;
Mohamed, Yahia A. ;
El-Bayouki, Khairy A. M. ;
Basyouni, Wahid M. ;
Abbas, Samir Y. .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2010, 45 (08) :3365-3373
[2]   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
[3]   A facile vanadium-catalyzed aerobic oxidative synthesis of quinazolinones from 2-aminobenzamides with aldehydes or alcohols [J].
Bie, Zhixing ;
Li, Guosong ;
Wang, Lianyue ;
Lv, Ying ;
Niu, Jingyang ;
Gao, Shuang .
TETRAHEDRON LETTERS, 2016, 57 (44) :4935-4938
[4]   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
[5]   Efficient and selective nitrile hydration reactions in water catalyzed by an unexpected dimethylsulfinyl anion generated in situ from CsOH and DMSO [J].
Chen, Haonan ;
Dai, Wujie ;
Chen, Yi ;
Xu, Qing ;
Chen, Jianhui ;
Yu, Lei ;
Zhao, Yajuan ;
Ye, Mingde ;
Pan, Yuanjiang .
GREEN CHEMISTRY, 2014, 16 (04) :2136-2141
[6]   Iron-catalyzed aerobic oxidative functionalization of sp3 C-H bonds: a versatile strategy for the construction of N-heterocycles [J].
Chen, Xiuling ;
Chen, Tieqiao ;
Ji, Fangyan ;
Zhou, Yongbo ;
Yin, Shuang-Feng .
CATALYSIS SCIENCE & TECHNOLOGY, 2015, 5 (04) :2197-2202
[7]  
Cheng R., 2013, SYNTHESIS-STUTTGART, P2998
[8]   Oxidant- and metal-free synthesis of 4(3H)-quinazolinones from 2-amino-N-methoxybenzamides and aldehydes via acid-promoted cyclocondensation and elimination [J].
Cheng, Ran ;
Tang, Linlin ;
Guo, Tianjian ;
Zhang-Negrerie, Daisy ;
Du, Yunfei ;
Zhao, Kang .
RSC ADVANCES, 2014, 4 (50) :26434-26438
[9]   Iron Nitrate/TEMPO: a Superior Homogeneous Catalyst for Oxidation of Primary Alcohols to Nitriles in Air [J].
Dighe, Shashikant U. ;
Chowdhury, Deepan ;
Batra, Sanjay .
ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (18) :3892-3896
[10]   Copper-Catalyzed Synthesis of 2-Arylquinazolinones from 2-Arylindoles with Amines or Ammoniums [J].
Feng, Yadong ;
Li, Yudong ;
Cheng, Guolin ;
Wang, Lianhui ;
Cui, Xiuling .
JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (14) :7099-7107
123456