An Improved Understanding of the Reaction of Bis(bromomethyl)quinoxaline 1-N-Oxides with Amines Using Substituent Effects

The reaction of bis(bromomethyl)quinoxaline N-oxides with amines is interesting from a reaction mechanism perspective and due to the reported biological activity of compounds in this general class. The complex mechanism of this reaction (particularly in the case of primary amines) is complicated fur...

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Bibliographic Details
Published in:Journal of organic chemistry 2007-04, Vol.72 (9), p.3186-3193
Main Authors: Evans, Kathryn M, Slawin, Alexandra M. Z, Lebl, Tomas, Philp, Douglas, Westwood, Nicholas J
Format: Article
Language:English
Subjects:
Amines - chemistry
Chemistry
Diethylamines - chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings
Kinetics and mechanisms
Organic chemistry
Oxides - chemistry
Preparations and properties
Quinoxalines - chemistry
Reactivity and mechanisms
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Summary:The reaction of bis(bromomethyl)quinoxaline N-oxides with amines is interesting from a reaction mechanism perspective and due to the reported biological activity of compounds in this general class. The complex mechanism of this reaction (particularly in the case of primary amines) is complicated further when C6 or C7 substituted mono-N-oxides are considered. In this study, the synthesis and subsequent characterization of a series of 2,3-bis(bromomethyl)quinoxaline 1-N-oxides is reported. Experimental and computational evidence is used to show that the observed product ratios from the reaction with diethylamine reflect the influence of both the C6/C7 substituent and the N-oxide functional group on the initial nucleophilic substitution reaction.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo062380y