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

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Hydroxylamines
Benzimidazoles
Imidazoles
Nitrogen Compounds
X ray analysis
Ultraviolet spectroscopy
Spectrum Analysis
X-Rays
nitrones

Keywords

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

Cite this

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title = "Reactions of hydroxylamines with ethyl cyanoformate - preparation of aminonitrones and their synthetic applications",
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.",
keywords = "NITROGEN HETEROCYCLES, HYDROXYLAMINE, ETHYL CYANOFORMATE, ALPHA-AMINONITRONE, Nitrogen heterocycles, α-Aminonitrone, Ethyl cyanoformate, Hydroxylamine",
author = "Branco, {Paula Cristina de S{\'e}rio} and Prabhakar, {Alberto Sundaresan} and Lobo, {Ana Maria F{\'e}lix Trindade} and Williams, {David Jeremy}",
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journal = "Tetrahedron",
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T1 - Reactions of hydroxylamines with ethyl cyanoformate - preparation of aminonitrones and their synthetic applications

AU - Branco, Paula Cristina de Sério

AU - Prabhakar, Alberto Sundaresan

AU - Lobo, Ana Maria Félix Trindade

AU - Williams, David Jeremy

PY - 1992/1/1

Y1 - 1992/1/1

N2 - 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.

AB - 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.

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KW - HYDROXYLAMINE

KW - ETHYL CYANOFORMATE

KW - ALPHA-AMINONITRONE

KW - Nitrogen heterocycles

KW - α-Aminonitrone

KW - Ethyl cyanoformate

KW - Hydroxylamine

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U2 - 10.1016/S0040-4020(01)88224-7

DO - 10.1016/S0040-4020(01)88224-7

M3 - Article

VL - 48

SP - 6335

EP - 6360

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

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