EventsThe 11th International Electronic Conference on Synthetic Organic Chemistry
Event submissions
Published
with-doi10.3390/ecsoc-11-01326
This submission belongs to the session a. General Organic Synthesis of the event The 11th International Electronic Conference on Synthetic Organic Chemistry
Published date
30 Nov, 2007
Citation
Nguyen Thi Thanh Mai, A. Monge, I. Aldana, S. Pérez-Silanes, B. Solano, E. Vicente, L. M. Lima, Unexpected Reduction of Ethyl 3-phenylquinoxaline-2-carboxylate 1,4-di-N-oxide Derivatives by Amines, in Proceedings of The 11th International Electronic Conference on Synthetic Organic Chemistry, 1 November–30 November 2007, MDPI: Basel, Switzerland, doi: 10.3390/ecsoc-11-01326
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Unexpected Reduction of Ethyl 3-phenylquinoxaline-2-carboxylate 1,4-di-N-oxide Derivatives by Amines

Nguyen Thi Thanh Mai 1
A. Monge 1
I. Aldana 1
S. Pérez-Silanes 1
B. Solano 1
E. Vicente 1
L. M. Lima 1,2
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
Abstract
The unexpected tendency of amines and functionalized hydrazines to reduce the ethyl 3-phenylquinoxaline-2-carboxylate 1,4-di-N-oxide (1) to a quinoxaline (1c) and mono-oxide quinoxalines (1a and 1b) is described. The experimental conditions were standardized in the use of 2 equivalents of amine in ethanol under reflux for 2 hours, with the aim of studying the distinct reductive profile of the amines and the chemoselectivity of the process. With the exception of hydrazine hydrate, which reduced compound 1 to a 3- phenyl-2-quinoxalinecarbohydrazide derivative, the amines only acted as reducing agents.
Keywords
quinoxaline N-oxides
reduction
carboxylate
amines
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