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