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

Paula Cristina de Sério Branco; Alberto Sundaresan Prabhakar; Ana Maria Félix Trindade Lobo; David Jeremy Williams

doi:10.1016/S0040-4020(01)88224-7

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

Paula Cristina de Sério Branco, Alberto Sundaresan Prabhakar, Ana Maria Félix Trindade Lobo, David Jeremy Williams

Research output: Contribution to journal › Article › peer-review

53 Citations (Scopus)

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 language	English
Pages (from-to)	6335-6360
Number of pages	26
Journal	Tetrahedron
Volume	48
Issue number	30
DOIs	https://doi.org/10.1016/S0040-4020(01)88224-7
Publication status	Published - 1 Jan 1992

Keywords

Nitrogen heterocycles
α-Aminonitrone
Ethyl cyanoformate
Hydroxylamine

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10.1016/S0040-4020(01)88224-7

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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\}",

year = "1992",

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doi = "10.1016/S0040-4020(01)88224-7",

language = "English",

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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.

KW - NITROGEN HETEROCYCLES

KW - HYDROXYLAMINE

KW - ETHYL CYANOFORMATE

KW - ALPHA-AMINONITRONE

KW - Nitrogen heterocycles

KW - α-Aminonitrone

KW - Ethyl cyanoformate

KW - Hydroxylamine

UR - https://www.scopus.com/pages/publications/0026740225

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

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

M3 - Article

SN - 0040-4020

VL - 48

SP - 6335

EP - 6360

JO - Tetrahedron

JF - Tetrahedron

IS - 30

ER -

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

Abstract

Keywords

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