2022-04-182022-04-182010-03-13Coşkun, N. ve Çetin, M. (2010). "Thermal rearrangements of tetrahydroimidazo[1,5-b]isoxazole-2,3-dicarboxylates. Synthesis of 3H-imidazol-1-ium ylides and their silver derivatives". Tetrahedron, 66(11), 2053-2060.0040-4020https://doi.org/10.1016/j.tet.2010.01.037https://www.sciencedirect.com/science/article/pii/S0040402010000694http://hdl.handle.net/11452/25826Isoxazolines 2 from the cycloaddition of imidazoline 3-oxides 1 with DMAD undergo rearrangement to 3,4-dihydro-2H-imidazol-1-ium-1-(1,2-bis-methoxycarbonyl-2-oxo-ethanides) 3, which spontaneously undergo elimination to give 3H-imidazol-1-ium-1-(1,2-bis-methoxycarbonyl-2-oxo-ethanides) 5 or 1H-imidazoles 6 when heated in toluene at reflux. The presence of the aromatic ring at C-6 decelerated the conversion and enhanced the yield of 5. Solvents more polar than toluene (e.g.. DMSO) provided quantitative conversion of 2 into 6 in mild conditions, while in less polar solvents such as CCl4, the reaction rate was lowered and the yield of 5 enhanced. C-2 unsubstituted ylides 5 were treated with Ag2O or AgNO3 in the presence of Et3N at room temperature to give C-2 metallated derivatives 9 in excellent yields.eninfo:eu-repo/semantics/closedAccessDipolar cycloadditionCyclic nitrones4-IsoxazolinesYlidesRearrangementNHCsAg(I) metallated imidazolium ylidesImıdazoline 3-oxidesDiastereoselective addition1,3-dipolar cycloadditionRegioReactivityComplexesChemistryArticle0002757064000142-s2.0-76449113187205320606611Chemistry, organicNitrones; Cycloaddition Reactions; Hydroxylamines(r) (s) 2 [(1r,2s,5r) 2 isopropyl 5 methylcyclohexyl] 3 methyl 5 (4 methoxyphenyl) 3a phenyl 3a,4,5,6 tetrahydroimidazo[1,5 b]isoxazole 2,3 dicarboxylate(r) (s) 2 [(1r,2s,5r) 2 isopropyl 5 methylcyclohexyl]3 methyl 3a phenyl 5 p tolyl 3a,4,5,6 tetrahydroimidazo[1,5 b]isoxazole 2,3 dicarboxylate1 (3,4 dimethoxyphenyl) 4 phenyl 1h imidazole; 1 (3,4 dimethoxyphenyl) 4 phenyl 2,5 dihydro 1h imidazole 3 oxide1 (4 bromophenyl) 4 phenyl 1h imidazole1 (4 chlorophenyl) 4 phenyl 1h imidazole1 (4 methoxyphenyl) 2,4 diphenyl 1h imidazole1 (4 methoxyphenyl) 4 phenyl 1h imidazole1,4 diphenyl 1h imidazole2 (3 nitrophenyl) 5 phenyl 3 p tolyl 3h imidazol 1 ium 1 (1,2 bis methoxycarbonyl 2 oxoethanide)2 (3,4 dimethoxyphenyl) 5 phenyl 3 p tolyl 3h imidazol 1 ium 1 (1,2 bis methoxycarbonyl 2 oxoethanide)2 (4 chlorophenyl) 5 phenyl 3 p tolyl 3h imidazol 1 ium 1 (1,2 bis methoxycarbonyl 2 oxoethanide)2,4 diphenyl 1 p tolyl 1h imidazole3 (3,4 dimethoxyphenyl) 5 phenyl 3h imidazol 1 ium 1 (1,2 bis methoxycarbonyl 2 oxoethanide)3 (4 bromophenyl) 5 phenyl 3h imidazol 1 ium 1 (1,2 bismethoxycarbonyl 2 oxoethanide)3 (4 chlorophenyl) 5 phenyl 3h imidazol 1 ium 1 (1,2 bismethoxycarbonyl 2 oxoethanide)3 (4 methoxyphenyl) 2,5 diphenyl 3h imidazol 1 ium 1 (1,2 bis methoxycarbonyl 2 oxoethanide)3 (4 methoxyphenyl) 5 phenyl 3h imidazol 1 ium 1 (1,2-bis methoxycarbonyl 2 oxoethanide)3 (p tolyl) 2 (4 methoxyphenyl) 5 phenyl 3h imidazol 1 ium 1 (1,2 bis methoxycarbonyl 2 oxoethanide)3 (p tolyl) 2,5 diphenyl 3h imidazol 1 ium 1 (1,2 bis methoxycarbonyl 2 oxoethanide)3,4 dihydro 2h imidazol 1 ium 1 (1,2 bis methoxycarbonyl 2 oxo ethanide)3,5 diphenyl 3h imidazol 1 ium 1 (1,2 bis methoxycarbonyl 2 oxoethanide)3h imidazol 1 ium 1 (1,2 bis methoxycarbonyl 2 oxo ethanide)4 phenyl 1 p tolyl 1h imidazole; 5 phenyl 3 p methoxyphenyl 3h imidazol 1 ium 1 [(1 methoxycarbonyl) 2 menthyloxycarbonyl] 2 oxoethanide5 phenyl 3 p tolyl 3h imidazol 1 ium 1 (1,2 bis methoxycarbonyl 2 oxoethanide)5 phenyl 3 p tolyl 3h imidazol 1 ium 1 [(1 methoxycarbonyl) 2 menthyloxycarbonyl] 2 oxoethanideImidazole derivativeIsoxazoline derivativeTolueneUnclassified drugArticleCycloadditionDrug synthesisPriority journalReaction analysisThermal analysis