An efficient construction of quinazolin-4(3H)-ones under microwave irradiation

被引:71
作者
Li, Feng [1 ]
Feng, Yiqing [1 ]
Meng, Qingqing [1 ]
Li, Wenhua [1 ]
Li, Zhiming [1 ]
Wang, Quanrui [1 ]
Tao, Fenggang [1 ]
机构
[1] Fudan Univ, Dept Chem, 220 Handan Rd, Shanghai 200433, Peoples R China
关键词
quinazolin-4(3H)-ones; microwave irradiation; Iressa;
D O I
10.3998/ark.5550190.0008.105
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The highly accelerated Niementowski synthesis of quinazolin- 4( 3H)- one and quinazolin- 2,4-dione derivatives under microwave irradiation is reported. Compared to the conventional conditions, this new method shows the advantages of a good substrate tolerance, and a clean and rapid conversion. The method has been successfully applied for the construction of the key intermediate of iressa.
引用
收藏
页码:40 / 50
页数:11
相关论文
共 47 条
[1]   Novel series of 8H-quinazolino[4,3-b]quinazolin-8-ones via two Niementowski condensations [J].
Alexandre, FR ;
Berecibar, A ;
Wrigglesworth, R ;
Besson, T .
TETRAHEDRON, 2003, 59 (09) :1413-1419
[2]   Microwave-assisted Niementowski reaction. Back to the roots [J].
Alexandre, FR ;
Berecibar, A ;
Besson, T .
TETRAHEDRON LETTERS, 2002, 43 (21) :3911-3913
[3]   SYNTHESIS AND IDENTIFICATION OF MAJOR METABOLITES OF PRAZOSIN FORMED IN DOG AND RAT [J].
ALTHUIS, TH ;
HESS, HJ .
JOURNAL OF MEDICINAL CHEMISTRY, 1977, 20 (01) :146-149
[4]  
[Anonymous], ADV HETEROCYCL CHEM
[5]   ZD1839 ('Iressa')1,2 as an anticancer agent [J].
Baselga, J ;
Averbuch, SD .
DRUGS, 2000, 60 (Suppl 1) :33-40
[6]   Solid-phase synthesis of 1,3-dialkyl quinazoline-2,4-diones [J].
Buckman, BO ;
Mohan, R .
TETRAHEDRON LETTERS, 1996, 37 (26) :4439-4442
[7]   Inhibition of insulin-like growth factor-1 receptor signaling enhances growth-inhibitory and proapoptotic effects of gefitinib (Iressa) in human breast cancer cells [J].
Camirand, A ;
Zakikhani, M ;
Young, F ;
Pollak, M .
BREAST CANCER RESEARCH, 2005, 7 (04) :R570-R579
[8]   An eco-efficient pilot plant scale synthesis of two 5-substituted-6,7-dimethoxy-1-H-quinazoline-2,4-diones [J].
Connolly, TJ ;
McGarry, P ;
Sukhtankar, S .
GREEN CHEMISTRY, 2005, 7 (08) :586-589
[9]   Microwaves in organic synthesis.: Thermal and non-thermal microwave effects [J].
de la Hoz, A ;
Díaz-Ortiz, A ;
Moreno, A .
CHEMICAL SOCIETY REVIEWS, 2005, 34 (02) :164-178
[10]   Microwave-assisted synthesis involving immobilized catalysts [J].
Desai, B ;
Kappe, CO .
IMMOBILIZED CATALYSTS: SOLID PHASES, IMMOBILIZATION AND APPLICATIONS, 2004, 242 :177-208