TY - JOUR
T1 - Formation of 2,3,6,8-tetraazabicyclo[3.2.1]oct-3-ene derivatives in reaction between 2-acyl-3-imidazoline 3-oxides and hydrazine and their oxidation to the corresponding nitroxyl radicals and 1,2,4-triazine 4-oxide
AU - Grigor'ev, I. A.
AU - Shchukin, G. I.
AU - Dikanov, S. A.
AU - Kuznetsova, I. K.
AU - Volodarskii, L. B.
PY - 1982/5
Y1 - 1982/5
N2 - 1. Reaction of 2-acyl-1-hydroxy-3-imidazoline 3-oxides with monosubstituted hydrazines leads to monosubstituted hydrazones, derivatives of 2-acyl-1-hydroxy-3-imidazoline 3-oxide, which on oxidation give stable nitroxyl radicals of the imidazoline series. 2. In the reaction between 2-acyl-3-imidazoline 3-oxides and hydrazine, an intramolecular cyclization takes place with the formation of a new heterocyclic system, 2,3,6,8-tetraazabicyclo[3.2.1]oct-3-ene. 3. The oxidation of 6,8-dihydroxy-4,5,7,7-tetraalkyl-1-R-2,3,6,8-tetraazabicyclo[3.2.1]oct-3-enes leads to bicyclic nitroxyl radicals, 8-hydroxy-4,5,7,7-tetraalkyl-1-R-2,3,6,8-tetraazabicyclo[3.2.1]oct-3-en-6 oxyls, which on oxidation give 1,2,4-triazine 4-oxides.
AB - 1. Reaction of 2-acyl-1-hydroxy-3-imidazoline 3-oxides with monosubstituted hydrazines leads to monosubstituted hydrazones, derivatives of 2-acyl-1-hydroxy-3-imidazoline 3-oxide, which on oxidation give stable nitroxyl radicals of the imidazoline series. 2. In the reaction between 2-acyl-3-imidazoline 3-oxides and hydrazine, an intramolecular cyclization takes place with the formation of a new heterocyclic system, 2,3,6,8-tetraazabicyclo[3.2.1]oct-3-ene. 3. The oxidation of 6,8-dihydroxy-4,5,7,7-tetraalkyl-1-R-2,3,6,8-tetraazabicyclo[3.2.1]oct-3-enes leads to bicyclic nitroxyl radicals, 8-hydroxy-4,5,7,7-tetraalkyl-1-R-2,3,6,8-tetraazabicyclo[3.2.1]oct-3-en-6 oxyls, which on oxidation give 1,2,4-triazine 4-oxides.
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U2 - 10.1007/BF00949952
DO - 10.1007/BF00949952
M3 - Article
AN - SCOPUS:34250225635
SN - 0568-5230
VL - 31
SP - 972
EP - 980
JO - Bulletin of the Academy of Sciences of the USSR Division of Chemical Science
JF - Bulletin of the Academy of Sciences of the USSR Division of Chemical Science
IS - 5
ER -