Microwave-assisted synthesis of bioactive quinazolines and quinazolinones

被引:46
作者
Besson, Thierry [1 ]
Chosson, Elizabeth [1 ]
机构
[1] Univ Rouen, INSA Rouen, CNRS UMR 6014, COBRA IRCOF,UFR Med Pharm, F-76183 Rouen 1, France
关键词
heterocycles; quinazolines; quinazolin-4-ones; natural products; bioactive compounds; microwave irradiation; graphite; solvent-free chemistry;
D O I
10.2174/138620707783220356
中图分类号
Q5 [生物化学];
学科分类号
071010 ; 081704 ;
摘要
This paper aims to review recent developments in the synthesis of quinazolines and quinazolinone derivatives under conditions that include the application of microwave heating in the ring forming step. Recently, two reviews on the synthesis and chemistry of natural and synthetic quinazolines and quinazolinones have been published. This review highlights significant examples where microwave heating has been either synthetically enabling or has provided a key advantage over conventional thermal methods. Wherever possible, this review will focus on chemistry carried out using mono-mode systems and well-designed type of instrumentation. The review is grouped according to the main heterocycle types in order of increasing complexity; commencing with quinazolines and their derivatives. The microwave-assisted synthesis of quinazolines and quinazolinones will be classified and based on the substitution patterns of the ring system. Syntheses of heterocyclic systems of particular biological or commercial interest are emphasized.
引用
收藏
页码:903 / 917
页数:15
相关论文
共 56 条
[31]   Rapid synthesis of 2,3-disubstituted-quinazolin-4-ones enhanced by microwave-assisted decomposition of formamide [J].
Kostakis, Ioannis K. ;
Elomri, Abdelhakim ;
Seguin, Elisabeth ;
Iannelli, Mauro ;
Besson, Thierry .
TETRAHEDRON LETTERS, 2007, 48 (38) :6609-6613
[32]   A catalyst- and solvent-free selective approach to biologically important quinazolines and benzo[g]quinazoline [J].
Kumar, V ;
Mohan, C ;
Gupta, M ;
Mahajan, MP .
TETRAHEDRON, 2005, 61 (14) :3533-3538
[33]   Structure-activity relationships of novel 2-substituted quinazoline antibacterial agents [J].
Kung, PP ;
Casper, MD ;
Cook, KL ;
Wilson-Lingardo, L ;
Risen, LM ;
Vickers, TA ;
Ranken, R ;
Blyn, LB ;
Wyatt, JR ;
Cook, PD ;
Ecker, DJ .
JOURNAL OF MEDICINAL CHEMISTRY, 1999, 42 (22) :4705-4713
[34]   Solvent-free synthesis of a series of differently N-substituted 4-amino-2-methylquinazolines under microwave irradiation [J].
Kurteva, VB ;
Zlatanova, VN ;
Dimitrov, VD .
ARKIVOC, 2006, :46-56
[35]   An efficient construction of quinazolin-4(3H)-ones under microwave irradiation [J].
Li, Feng ;
Feng, Yiqing ;
Meng, Qingqing ;
Li, Wenhua ;
Li, Zhiming ;
Wang, Quanrui ;
Tao, Fenggang .
ARKIVOC, 2007, :40-50
[36]   Microwave assisted organic synthesis -: a review [J].
Lidström, P ;
Tierney, J ;
Wathey, B ;
Westman, J .
TETRAHEDRON, 2001, 57 (45) :9225-9283
[37]   Microwave assisted synthesis of N-arylheterocyclic substituted-4-aminoquinazoline derivatives [J].
Liu, Gang ;
Yang, Song ;
Song, Baoan ;
Xue, Wei ;
Hu, Deyu ;
Jin, Linhong ;
Lu, Ping .
MOLECULES, 2006, 11 (04) :272-278
[38]   Design and synthesis of a quinazolinone natural product-templated library with cytotoxic activity [J].
Liu, JF ;
Kaselj, M ;
Isome, Y ;
Ye, P ;
Sargent, K ;
Sprague, K ;
Cherrak, D ;
Wilson, CJ ;
Si, Y ;
Yohannes, D ;
Ng, SC .
JOURNAL OF COMBINATORIAL CHEMISTRY, 2006, 8 (01) :7-10
[39]   Microwave-assisted concise total syntheses of quinazolinobenzodiazepine alkaloids [J].
Liu, JF ;
Kaselj, M ;
Isome, Y ;
Chapnick, J ;
Zhang, BL ;
Bi, G ;
Yohannes, D ;
Yu, LB ;
Baldino, CM .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (25) :10488-10493
[40]   Microwave-assisted one-pot synthesis of 2,3-disubstituted 3H-quinazolin-4-ones [J].
Liu, JF ;
Lee, JY ;
Dalton, AM ;
Bi, G ;
Yu, LB ;
Baldino, CM ;
McElory, E ;
Brown, M .
TETRAHEDRON LETTERS, 2005, 46 (08) :1241-1244