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Molecules 2008, 13(1), 78-85; doi:10.3390/molecules13010078

Unexpected Reduction of Ethyl 3-Phenylquinoxaline-2- carboxylate 1,4-Di-N-oxide Derivatives by Amines

1
Unidad en Investigación y Desarrollo de Medicamentos, Centro de Investigación en Farmacobiología Aplicada (CIFA), University of Navarra, 31080 Pamplona, Spain
2
Laboratório de Avaliação e Síntese de Substâncias Bioativas (LASSBio), Faculdade de Farmácia, Universidade Federal do Rio de Janeiro (UFRJ), Rio de Janeiro, PO Box 68024, RJ 21944-970, Brazil
*
Author to whom correspondence should be addressed.
Received: 21 December 2007 / Revised: 16 January 2008 / Accepted: 16 January 2008 / Published: 17 January 2008
(This article belongs to the Special Issue ECSOC-11)
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Abstract

The unexpected tendency of amines and functionalized hydrazines to reduceethyl 3-phenylquinoxaline-2-carboxylate 1,4-di-N-oxide (1) to afford a quinoxaline 1c andmono-oxide quinoxalines 1a and 1b is described. The experimental conditions werestandardized to the use of two equivalents of amine in ethanol under reflux for two hours,with the aim of studying the distinct reductive profiles of the amines and thechemoselectivity of the process. With the exception of hydrazine hydrate, which reducedcompound 1 to a 3-phenyl-2-quinoxalinecarbohydrazide derivative, the amines only actedas reducing agents.
Keywords: Quinoxaline N-oxides; reduction; carboxylate; amines. Quinoxaline N-oxides; reduction; carboxylate; amines.
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

Lima, L.M.; Vicente, E.; Solano, B.; Pérez-Silanes, S.; Aldana, I.; Monge, A. Unexpected Reduction of Ethyl 3-Phenylquinoxaline-2- carboxylate 1,4-Di-N-oxide Derivatives by Amines. Molecules 2008, 13, 78-85.

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