An improved understanding of the reaction of bis(bromomethyl)quinoxaline 1-N-oxides with amines using substituent effects

Kathryn M. Evans, Alexandra M.Z. Slawin, Tomas Lebl, Douglas Philp, Nicholas J. Westwood*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

6 Scopus citations

Abstract

(Chemical Equation Presented) 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.

Original languageEnglish (US)
Pages (from-to)3186-3193
Number of pages8
JournalJournal of Organic Chemistry
Volume72
Issue number9
DOIs
StatePublished - Apr 27 2007

ASJC Scopus subject areas

  • Organic Chemistry

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