1218942-58-5Relevant articles and documents
Intramolecular 1,3-Dipolar cycloaddition of alkenylnitrones of the 4 H-Imidazole series: Synthesis of a new nitroxide pH-sensitive spin probe
Morozov, Denis A.,Kirilyuk, Igor A.,Gatilov, Yuri V.,Bagryanskaya, Irina Yu.,Bozhko, Julya Yu.,Komarov, Denis A.,Grigorev, Igor A.
experimental part, p. 343 - 348 (2010/03/24)
A new method was used for the preparation of a pH-sensitive spin probe involving an intramolecular 1,3-dipolar cycloaddition-reductive isoxazolidine ring-opening-oxidation reaction sequence. 2-(2-Allyloxyphenyl)-5-R-4,4-dimethyl- 4H-imidazole-3-oxides (R=Me, NMe, prepared from 3-hydroxylamino-3-methylbutan-2- one, undergo intramolecular 1,3-dipolar cycloaddition upon heating in toluene. Treatment of the cycloadducts with low-valence titanium (LVT) reagent resulted in reductive cleavage of the N-O bond of the isoxazolidine ring to give 3-hydroxymethyl-5,5-dimethyl-4-R-2,5-dihydrospiro[imidazol-2,4-chromane]s. The amine (R=NMe was then oxidized with MCPBA to the target nitroxide-3- hydroxymethyl-5,5-dimethyl-4-dimethylamino-2,5-dihydrospiro[imidazole-2, 4-chroman]-1-oxyl. Georg Thieme Verlag Stuttgart.