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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 which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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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