Microwave assisted synthesis of 2'-/3'-azaflavones/azaflavonones and their N-alkyl derivatives

被引:0
作者
Yasar, Ahmet [1 ]
Ulas, Nevin [1 ]
Yildirim, Sercan [1 ]
机构
[1] Karadeniz Tech Univ, Fac Pharm, TR-61080 Trabzon, Turkey
关键词
Azaflavone; azaflavonone; microwave; azachalcone;
D O I
暂无
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
2'-Azaflavonone (6) and 3'-azaflavonone (7); were synthesized by a simple environmentally friendly microwave-assisted one-pot method for the cyclization of 2'-hydroxy beta'-2-azachalcanon-beta-ol (1), 2'-hydroxy (E)-2-azachalcone (2), 2'-hydroxy (E)-3-azachalcone (3) under solventless conditions using K-10 clay. In addition to these synthesis, 3-(pyridin-2-yl methyl)-2'-azaflavone (8) and 3-(pyridin-3-yl methyl)-3'-azaflavone (9) were synthesized using silica-supported sodium hydrogen sulphate then the treatment with base, respectively. Additionally, for antimicrobial activities N-alkyl substituted 3'-azaflavonium and 2'-azaflavonium bromides (1012) were prepared from compounds 3, 4 -5 and 8 -9.
引用
收藏
页码:73 / 81
页数:9
相关论文
共 18 条
[1]   Alumina supported-CeCl3•7H2O-NaI:: an efficient catalyst for the cyclization f 2′-aminochalcones to the corresponding 2-aryl-2,3-dihydroquinolin-4(1H)-ones under solvent free conditions [J].
Ahmed, Naseem ;
van Lier, Johan E. .
TETRAHEDRON LETTERS, 2007, 48 (01) :13-15
[2]  
ANNIGERI AC, 1964, INDIAN J CHEM, V2, P413
[3]   SYNTHESE EINIGER BIOLOGISCH INTERESSANTER 4]-AZAFLAVONOIDE [J].
ANNIGERI, AC ;
SIDDAPPA, S .
MONATSHEFTE FUR CHEMIE UND VERWANDTE TEILE ANDERER WISSENSCHAFTEN, 1965, 96 (02) :625-&
[4]   CHALCONE DERIVATIVES AS PRECURSORS OF 1,2,3,4-TETRAHYDRO-4-QUINOLONES [J].
DONNELLY, JA ;
FARRELL, DF .
TETRAHEDRON, 1990, 46 (03) :885-894
[5]   INHIBITION OF MYELOPEROXIDASE RELEASE FROM RAT POLYMORPHONUCLEAR LEUKOCYTES BY A SERIES OF AZACHALCONE DERIVATIVES [J].
EDWARDS, ML ;
STEMERICK, DM ;
SABOL, JS ;
DIEKEMA, KA ;
DINERSTEIN, RJ .
JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (25) :4357-4362
[6]  
Harborne J. B, 1988, FLAVONOIDS ADV RES
[7]   An environmentally benign synthesis of flavones from 1,3-diketones using silica gel supported NaHSO4 catalyst [J].
Kucukislamoglu, M ;
Nebioglu, M ;
Zengin, M ;
Arslan, M ;
Yayli, N .
JOURNAL OF CHEMICAL RESEARCH, 2005, (09) :556-557
[8]   A simple and facile solventless procedure for the cyclization of 2′-amino- and 2′-hydroxy-chalcones using silica-supported sodium hydrogen sulphate as heterogenous catalyst [J].
Kumar, K. Hemanth ;
Perumal, P. T. .
CANADIAN JOURNAL OF CHEMISTRY, 2006, 84 (08) :1079-1083
[9]  
Loupy A., 2002, MICROWAVES ORGANIC S
[10]   Antimicrobial activity of some N-alkyl substituted of (E)-4-azachalconium and (E)-3′-hydroxy-4-azachalconium bromides [J].
Nowakowska, Z ;
Wyrzykiewicz, E ;
Kedzia, B .
FARMACO, 2002, 57 (08) :657-661