Substitutions of Fluorine Atoms and Phenoxy Groups in the Synthesis of Quinoxaline 1,4-di-N-oxide Derivatives

doi:10.3390/molecules13010086

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Molecules 2008, 13(1), 86-95; doi:10.3390/molecules13010086

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Substitutions of Fluorine Atoms and Phenoxy Groups in the Synthesis of Quinoxaline 1,4-di-N-oxide Derivatives

Esther Vicente, Raquel Villar, Asunción Burguete, Beatriz Solano, Saioa Ancizu, Silvia Pérez-Silanes, Ignacio Aldana* and Antonio Monge

Unidad de Investigación y Desarrollo de Medicamentos, Centro de Investigación en Farmacobiología Aplicada (CIFA), University of Navarra, 31080 Pamplona, Spain

* Author to whom correspondence should be addressed.

Received: 18 December 2007; in revised form: 16 January 2008 / Accepted: 16 January 2008 / Published: 18 January 2008

(This article belongs to the Special Issue ECSOC-11)

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Abstract: The unexpected substitution of fluorine atoms and phenoxy groups attached toquinoxaline 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 replacedby a methoxy group when dissolved in an ammonia saturated solution of methanol wasclearly demonstrated. In addition, 2-phenoxyquinoxaline 1,4-di-N-oxide derivativesbecame 2-aminoquinoxaline 1,4-di-N-oxide derivatives in the presence of gaseousammonia.

Keywords: Quinoxaline; N-oxides; Beirut reaction; gaseous ammonia.

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MDPI and ACS Style

Vicente, E.; Villar, R.; Burguete, A.; Solano, B.; Ancizu, S.; Pérez-Silanes, S.; Aldana, I.; Monge, A. Substitutions of Fluorine Atoms and Phenoxy Groups in the Synthesis of Quinoxaline 1,4-di-N-oxide Derivatives. Molecules 2008, 13, 86-95.

AMA Style

Vicente E, Villar R, Burguete A, Solano B, Ancizu S, Pérez-Silanes S, Aldana I, Monge A. Substitutions of Fluorine Atoms and Phenoxy Groups in the Synthesis of Quinoxaline 1,4-di-N-oxide Derivatives. Molecules. 2008; 13(1):86-95.

Chicago/Turabian Style

Vicente, Esther; Villar, Raquel; Burguete, Asunción; Solano, Beatriz; Ancizu, Saioa; Pérez-Silanes, Silvia; Aldana, Ignacio; Monge, Antonio. 2008. "Substitutions of Fluorine Atoms and Phenoxy Groups in the Synthesis of Quinoxaline 1,4-di-N-oxide Derivatives." Molecules 13, no. 1: 86-95.

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