Substitutions of fluorine atoms and phenoxy groups in the synthesis of quinoxaline 1,4-di-N-oxide derivatives

被引:10
作者
Vicente, Esther [1 ]
Villar, Raquel [1 ]
Burguete, Asuncion [1 ]
Solano, Beatriz [1 ]
Ancizu, Saioa [1 ]
Perez-Silanes, Silvia [1 ]
Aldana, Ignacio [1 ]
Monge, Antonio [1 ]
机构
[1] Univ Navarra, CIFA, Unidad Invest & Desarrollo Medicamentos, E-31080 Pamplona, Spain
关键词
quinoxaline; N-oxides; Beirut reaction; gaseous ammonia;
D O I
10.3390/molecules13010086
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
The unexpected substitution of fluorine atoms and phenoxy groups attached to quinoxaline or benzofuroxan rings is described. The synthesis of 2-benzyl- and 2-phenoxy-3-methylquinoxaline 1,4-di-N-oxide derivatives was based on the classical Beirut reaction. The tendency of fluorine atoms linked to quinoxaline or benzofuroxan rings to be replaced by a methoxy group when dissolved in an ammonia saturated solution of methanol was clearly demonstrated. In addition, 2-phenoxyquinoxaline 1,4-di-N-oxide derivatives became 2-aminoquinoxaline 1,4-di-N-oxide derivatives in the presence of gaseous ammonia.
引用
收藏
页码:86 / 95
页数:10
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