胺对3-苯基喹喔啉-2-羧酸乙酯1,4-二氧化物衍生物的意外还原反应

Unexpected reduction of ethyl 3-phenylquinoxaline-2- carboxylate 1,4-di-N-oxide derivatives by amines.

作者信息

Lima Lidia M, Vicente Esther, Solano Beatriz, Pérez-Silanes Silvia, Aldana Ignacio, Monge Antonio

机构信息

Unidad en Investigación y Desarrollo de Medicamentos, Centro de Investigación en Farmacobiología Aplicada (CIFA), University of Navarra, 31080 Pamplona, Spain.

出版信息

Molecules. 2008 Jan 17;13(1):78-85. doi: 10.3390/molecules13010078.

DOI:10.3390/molecules13010078

PMID:18259131

原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6245414/

Abstract

The unexpected tendency of amines and functionalized hydrazines to reduce ethyl 3-phenylquinoxaline-2-carboxylate 1,4-di-N-oxide (1) to afford a quinoxaline 1c and mono-oxide quinoxalines 1a and 1b is described. The experimental conditions were standardized 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 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.

摘要

本文描述了胺类和官能化肼类将3-苯基喹喔啉-2-羧酸乙酯1,4-二-N-氧化物（1）还原为喹喔啉1c以及单氧化物喹喔啉1a和1b的意外趋势。实验条件被标准化为在乙醇中使用两当量的胺，回流两小时，目的是研究胺类的不同还原特性以及该过程的化学选择性。除水合肼将化合物1还原为3-苯基-2-喹喔啉甲酰肼衍生物外，胺类仅作为还原剂起作用。