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

详细信息    查看全文

• 作者：Kathryn M. Evans ; Alexandra M. Z. Slawin ; Tomas Lebl ; Douglas Philp ; Nicholas J. Westwood
• 刊名：Journal of Organic Chemistry
• 出版年：2007
• 出版时间：April 27, 2007
• 年：2007
• 卷：72
• 期：9
• 页码：3186 - 3193
• 全文大小：233K
• 年卷期：v.72,no.9(April 27, 2007)
• ISSN：1520-6904

文摘

jo062380yn00001>

journals/joceah/72/i09/figures/jo062380yn00001.gif" ALIGN="left" HSPACE=5>

The reaction of bis(bromomethyl)quinoxaline N-oxides with amines is interesting from a reactionmechanism 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 complicatedfurther when C6 or C7 substituted mono-N-oxides are considered. In this study, the synthesis andsubsequent 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 thereaction with diethylamine reflect the influence of both the C6/C7 substituent and the N-oxide functionalgroup on the initial nucleophilic substitution reaction.