QUINOXALINE DERIVATIVES: VIII. THE EFFECT OF ELECTRON-DONATING GROUPS ON THE FORMATION OF CERTAIN QUINOXALINECARBOXYANILIDE N-OXIDES AND THEIR REARRANGEMENT

Introduction of methyl or methoxy groups into the benzene ring of quinoxalinecarboxyanilide (Id), makes the resulting anilides less prone to "abnormal" oxidation (1). Normal N-oxides (IIf and IIj) were obtained from the anilides If and Ij in which the cyclic was unprotected. The methyl-sub...

Full description

Saved in:
Bibliographic Details
Published in:Canadian journal of chemistry 1965-12, Vol.43 (12), p.3424-3428
Main Authors: Ahmad, Yusuf, Habib, M. S, Iqbal, M, Qureshi, M. Ikram
Format: Article
Language:English
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Introduction of methyl or methoxy groups into the benzene ring of quinoxalinecarboxyanilide (Id), makes the resulting anilides less prone to "abnormal" oxidation (1). Normal N-oxides (IIf and IIj) were obtained from the anilides If and Ij in which the cyclic was unprotected. The methyl-substituted anilides Ig and Ih, however, on oxidation with peracetic acid gave the hydroxy derivatives (Vg and Vh) instead of the N-oxides (IIg and IIh). The methoxy-substituted anilides Ik and Il did not give the hydroxy derivatives Vk and Vl nor the expected N-oxides IIk and IIl. All the N-oxides (IIe, IIf, IIi, and IIj) on rearrangement with sulfuric acid yielded the corresponding amines IVe, IVf, IVi, and IVj. In spite of the slow rate of rearrangement of these N-oxides, attempts to isolate the intermediate hydroxyaminospirolactams (III) were unsuccessful.
ISSN:0008-4042
1480-3291
DOI:10.1139/v65-475