Reactions of hydroxylamines with ethyl cyanoformate - preparation of aminonitrones and their synthetic applications

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Abstract

The reaction of hydroxylamines with ethyl cyanoformate 1 leads to the formation of carbethoxyamino nitrones 2. UV spectroscopy provided information that suggested the nitrone structure for these compounds in solution. X-ray analysis of 2a confirmed that it exists entirely in the nitrone form in the solid state. These nitrones are shown to be excellent starring materials for a variety of nitrogen containg compounds, namely, imidazoles. benzimidazoles, benzimidazolones, oxadiazolones, N-arylamidines and quinoxalone.
Original languageEnglish
Pages (from-to)6335-6360
Number of pages26
JournalTetrahedron
Volume48
Issue number30
DOIs
Publication statusPublished - 1 Jan 1992

Keywords

  • Nitrogen heterocycles
  • α-Aminonitrone
  • Ethyl cyanoformate
  • Hydroxylamine

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