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Unexpected Reduction of Ethyl 3-Phenylquinoxaline-2- carboxylate 1,4-Di-N-oxide Derivatives by Amines
Molecules 2008, 13(1), 86-95; doi:10.3390/molecules13010086

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

, , , , , , *  and
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 / Revised: 16 January 2008 / Accepted: 16 January 2008 / Published: 18 January 2008
(This article belongs to the Special Issue ECSOC-11)
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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. Quinoxaline; N-oxides; Beirut reaction; gaseous ammonia.
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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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.

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