Synthesis of quinazolinones from anthranilamides and aldehydes via metal-free aerobic oxidation in DMSO

被引:158
作者
Kim, Na Yeun [1 ]
Cheon, Cheol-Hong [1 ]
机构
[1] Korea Univ, Dept Chem, Seoul 136701, South Korea
基金
新加坡国家研究基金会;
关键词
Quinazolinones; Aerobic oxidation; DMSO; Anthranilamide; One-pot synthesis; ONE-POT CONVERSION; EFFICIENT; DERIVATIVES; CATALYST; RECEPTOR; BENIGN; DESIGN;
D O I
10.1016/j.tetlet.2014.02.065
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A highly environmentally benign protocol for the synthesis of quinazolinones from anthranilamides and aldehydes via aerobic oxidation was developed in wet DMSO. This protocol is operationally simple, exhibits broad substrate scope, and does not need toxic metal catalysts and bases. In addition, the utility of this transformation was further demonstrated by converting the resulting quinazolinones into other useful products in the same-pot without their isolation. (C) 2014 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2340 / 2344
页数:5
相关论文
共 36 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]   One-Pot Three-Component Synthesis of 4(3H)-Quinazolinones from Benzyl Halides, Isatoic Anhydride, and Primary Amines [J].
Adib, Mehdi ;
Sheikhi, Ehsan ;
Bijanzadeh, Hamid Reza .
SYNLETT, 2012, 23 (01) :85-88
[3]   Design, synthesis and biological evaluation of novel quinazoline derivatives as potential anti-cancer agents [J].
Alafeefy, Ahmed M. ;
Ashour, Abdelkader E. .
JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY, 2012, 27 (04) :541-545
[4]  
[Anonymous], 2018, WATER AIR SOIL POLL, V147, P20, DOI [10.1016/j, DOI 10.1016/J, DOI 10.1371/J0URNAL.P0NE.0045405
[5]  
]
[6]  
Backvall J.-E., 2010, MODERN OXIDATION MET
[7]   Microwave activated synthesis of 2-aryl-qlainazolin-4(3H) ones [J].
Bakavoli, M. ;
Sabzevari, O. ;
Rahimizadeh, M. .
CHINESE CHEMICAL LETTERS, 2007, 18 (12) :1466-1468
[8]   One pot synthesis of 4(3H)-quinazolinones [J].
Bhat, BA ;
Sahu, DP .
SYNTHETIC COMMUNICATIONS, 2004, 34 (12) :2169-2176
[9]   Radical reactions with 3H-quinazolin-4-ones:: synthesis of deoxyvasicinone, mackinazolinone, luotonin A, rutaecarpine and tryptanthrin [J].
Bowman, W. Russell ;
Elsegood, Mark R. J. ;
Stein, Tobias ;
Weaver, George W. .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2007, 5 (01) :103-113
[10]   Cyanide as a powerful catalyst for facile synthesis of benzofused heteroaromatic compounds via aerobic oxidation [J].
Cho, Yeon-Ho ;
Lee, Chun-Young ;
Cheon, Cheol-Hong .
TETRAHEDRON, 2013, 69 (32) :6565-6573