Next Article in Journal / Special Issue
Substitutions of Fluorine Atoms and Phenoxy Groups in the Synthesis of Quinoxaline 1,4-di-N-oxide Derivatives
Previous Article in Journal / Special Issue
Synthesis and Antiplasmodial Activity of 3-Furyl and 3-Thienylquinoxaline-2-carbonitrile 1,4-Di-N-oxide Derivatives
Molecules 2008, 13(1), 78-85; doi:10.3390/molecules13010078
Article

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

1, 1, 1, 1, 1,*  and 1
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)
Download PDF [55 KB, uploaded 18 June 2014]

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

Share & Cite This Article

Export to BibTeX |
EndNote


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.

View more citation formats

Related Articles

Article Metrics

Comments

Citing Articles

[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert