Thermal rearrangements of tetrahydroimidazo[1,5-b]isoxazole-2,3-dicarboxylates. Synthesis of 3H-imidazol-1-ium ylides and their silver derivatives

dc.contributor.buuauthorCoşkun, Necdet
dc.contributor.buuauthorÇetin, Meliha
dc.contributor.departmentUludağ Üniversitesi/Fen-Edebiyat Fakültesi/Kimya Bölümü.tr_TR
dc.contributor.scopusid7004177880tr_TR
dc.contributor.scopusid7101935493tr_TR
dc.date.accessioned2022-04-18T07:36:39Z
dc.date.available2022-04-18T07:36:39Z
dc.date.issued2010-03-13
dc.description.abstractIsoxazolines 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.en_US
dc.identifier.citationCoşkun, 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.en_US
dc.identifier.endpage2060tr_TR
dc.identifier.issn0040-4020
dc.identifier.issue11tr_TR
dc.identifier.scopus2-s2.0-76449113187tr_TR
dc.identifier.startpage2053tr_TR
dc.identifier.urihttps://doi.org/10.1016/j.tet.2010.01.037
dc.identifier.urihttps://www.sciencedirect.com/science/article/pii/S0040402010000694
dc.identifier.urihttp://hdl.handle.net/11452/25826
dc.identifier.volume66tr_TR
dc.identifier.wos000275706400014tr_TR
dc.indexed.scopusScopusen_US
dc.indexed.wosSCIEen_US
dc.language.isoenen_US
dc.publisherPergamon-Elsevier Scienceen_US
dc.relation.journalTetrahedronen_US
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergitr_TR
dc.relation.tubitak107T840tr_TR
dc.rightsinfo:eu-repo/semantics/closedAccessen_US
dc.subjectDipolar cycloadditionen_US
dc.subjectCyclic nitronesen_US
dc.subject4-Isoxazolinesen_US
dc.subjectYlidesen_US
dc.subjectRearrangementen_US
dc.subjectNHCsen_US
dc.subjectAg(I) metallated imidazolium ylidesen_US
dc.subjectImıdazoline 3-oxidesen_US
dc.subjectDiastereoselective additionen_US
dc.subject1,3-dipolar cycloadditionen_US
dc.subjectRegioen_US
dc.subjectReactivityen_US
dc.subjectComplexesen_US
dc.subjectChemistryen_US
dc.subject.emtree(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 dicarboxylateen_US
dc.subject.emtree(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 dicarboxylateen_US
dc.subject.emtree1 (3,4 dimethoxyphenyl) 4 phenyl 1h imidazole; 1 (3,4 dimethoxyphenyl) 4 phenyl 2,5 dihydro 1h imidazole 3 oxideen_US
dc.subject.emtree1 (4 bromophenyl) 4 phenyl 1h imidazoleen_US
dc.subject.emtree1 (4 chlorophenyl) 4 phenyl 1h imidazoleen_US
dc.subject.emtree1 (4 methoxyphenyl) 2,4 diphenyl 1h imidazoleen_US
dc.subject.emtree1 (4 methoxyphenyl) 4 phenyl 1h imidazoleen_US
dc.subject.emtree1,4 diphenyl 1h imidazoleen_US
dc.subject.emtree2 (3 nitrophenyl) 5 phenyl 3 p tolyl 3h imidazol 1 ium 1 (1,2 bis methoxycarbonyl 2 oxoethanide)en_US
dc.subject.emtree2 (3,4 dimethoxyphenyl) 5 phenyl 3 p tolyl 3h imidazol 1 ium 1 (1,2 bis methoxycarbonyl 2 oxoethanide)en_US
dc.subject.emtree2 (4 chlorophenyl) 5 phenyl 3 p tolyl 3h imidazol 1 ium 1 (1,2 bis methoxycarbonyl 2 oxoethanide)en_US
dc.subject.emtree2,4 diphenyl 1 p tolyl 1h imidazoleen_US
dc.subject.emtree3 (3,4 dimethoxyphenyl) 5 phenyl 3h imidazol 1 ium 1 (1,2 bis methoxycarbonyl 2 oxoethanide)en_US
dc.subject.emtree3 (4 bromophenyl) 5 phenyl 3h imidazol 1 ium 1 (1,2 bismethoxycarbonyl 2 oxoethanide)en_US
dc.subject.emtree3 (4 chlorophenyl) 5 phenyl 3h imidazol 1 ium 1 (1,2 bismethoxycarbonyl 2 oxoethanide)en_US
dc.subject.emtree3 (4 methoxyphenyl) 2,5 diphenyl 3h imidazol 1 ium 1 (1,2 bis methoxycarbonyl 2 oxoethanide)en_US
dc.subject.emtree3 (4 methoxyphenyl) 5 phenyl 3h imidazol 1 ium 1 (1,2-bis methoxycarbonyl 2 oxoethanide)en_US
dc.subject.emtree3 (p tolyl) 2 (4 methoxyphenyl) 5 phenyl 3h imidazol 1 ium 1 (1,2 bis methoxycarbonyl 2 oxoethanide)en_US
dc.subject.emtree3 (p tolyl) 2,5 diphenyl 3h imidazol 1 ium 1 (1,2 bis methoxycarbonyl 2 oxoethanide)en_US
dc.subject.emtree3,4 dihydro 2h imidazol 1 ium 1 (1,2 bis methoxycarbonyl 2 oxo ethanide)en_US
dc.subject.emtree3,5 diphenyl 3h imidazol 1 ium 1 (1,2 bis methoxycarbonyl 2 oxoethanide)en_US
dc.subject.emtree3h imidazol 1 ium 1 (1,2 bis methoxycarbonyl 2 oxo ethanide)en_US
dc.subject.emtree4 phenyl 1 p tolyl 1h imidazole; 5 phenyl 3 p methoxyphenyl 3h imidazol 1 ium 1 [(1 methoxycarbonyl) 2 menthyloxycarbonyl] 2 oxoethanideen_US
dc.subject.emtree5 phenyl 3 p tolyl 3h imidazol 1 ium 1 (1,2 bis methoxycarbonyl 2 oxoethanide)en_US
dc.subject.emtree5 phenyl 3 p tolyl 3h imidazol 1 ium 1 [(1 methoxycarbonyl) 2 menthyloxycarbonyl] 2 oxoethanideen_US
dc.subject.emtreeImidazole derivativeen_US
dc.subject.emtreeIsoxazoline derivativeen_US
dc.subject.emtreeTolueneen_US
dc.subject.emtreeUnclassified drugen_US
dc.subject.emtreeArticleen_US
dc.subject.emtreeCycloadditionen_US
dc.subject.emtreeDrug synthesisen_US
dc.subject.emtreePriority journalen_US
dc.subject.emtreeReaction analysisen_US
dc.subject.emtreeThermal analysisen_US
dc.subject.scopusNitrones; Cycloaddition Reactions; Hydroxylaminesen_US
dc.subject.wosChemistry, organicen_US
dc.titleThermal rearrangements of tetrahydroimidazo[1,5-b]isoxazole-2,3-dicarboxylates. Synthesis of 3H-imidazol-1-ium ylides and their silver derivativesen_US
dc.typeArticle
dc.wos.quartileQ1en_US

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