Substitutions of fluorine atoms and phenoxy groups in the synthesis of quinoxaline 1,4-di-N-oxide derivatives.
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.
Vicente
Esther
E
Unidad de Investigación y Desarrollo de Medicamentos, Centro de Investigación en Farmacobiología Aplicada (CIFA), University of Navarra, 31080 Pamplona, Spain.
Villar
Raquel
R
Burguete
Asunción
A
Solano
Beatriz
B
Ancizu
Saioa
S
Pérez-Silanes
Silvia
S
Aldana
Ignacio
I
Monge
Antonio
A
D000995:Antitubercular Agents / Q000737:chemistry; D005461:Fluorine / Q000737:chemistry*; D013058:Mass Spectrometry; D010636:Phenols / Q000737:chemistry*; D011810:Quinoxalines / Q000138:chemical synthesis* / Q000737:chemistry
D000995:Antitubercular Agents; D010636:Phenols; D011810:Quinoxalines; D005461:Fluorine; C003282:quindoxin