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

Molecules

Lidia M. Lima¹  Esther Vicente¹  Beatriz Solano¹  Silvia Pérez-Silanes¹  Ignacio Aldana¹ 

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

关键词: Quinoxaline N-oxides;    reduction;    carboxylate;    amines;   

DOI  :  10.3390/molecules13010078

来源: mdpi

【 摘 要 】

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.

【 授权许可】

Unknown   
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