TY - JOUR
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 - http://www.scopus.com/record/display.uri?eid=2-s2.0-0026740225&origin=resultslist&sort=plf-f&src=s&st1
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 -