Thermal rearrangements of tetrahydroimidazo[1,5-b]isoxazole-2,3-dicarboxylates. Synthesis of 3H-imidazol-1-ium ylides and their silver derivatives
dc.contributor.buuauthor | Coşkun, Necdet | |
dc.contributor.buuauthor | Çetin, Meliha | |
dc.contributor.department | Uludağ Üniversitesi/Fen-Edebiyat Fakültesi/Kimya Bölümü. | tr_TR |
dc.contributor.scopusid | 7004177880 | tr_TR |
dc.contributor.scopusid | 7101935493 | tr_TR |
dc.date.accessioned | 2022-04-18T07:36:39Z | |
dc.date.available | 2022-04-18T07:36:39Z | |
dc.date.issued | 2010-03-13 | |
dc.description.abstract | Isoxazolines 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.citation | Coşkun, 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.endpage | 2060 | tr_TR |
dc.identifier.issn | 0040-4020 | |
dc.identifier.issue | 11 | tr_TR |
dc.identifier.scopus | 2-s2.0-76449113187 | tr_TR |
dc.identifier.startpage | 2053 | tr_TR |
dc.identifier.uri | https://doi.org/10.1016/j.tet.2010.01.037 | |
dc.identifier.uri | https://www.sciencedirect.com/science/article/pii/S0040402010000694 | |
dc.identifier.uri | http://hdl.handle.net/11452/25826 | |
dc.identifier.volume | 66 | tr_TR |
dc.identifier.wos | 000275706400014 | tr_TR |
dc.indexed.scopus | Scopus | en_US |
dc.indexed.wos | SCIE | en_US |
dc.language.iso | en | en_US |
dc.publisher | Pergamon-Elsevier Science | en_US |
dc.relation.journal | Tetrahedron | en_US |
dc.relation.publicationcategory | Makale - Uluslararası Hakemli Dergi | tr_TR |
dc.relation.tubitak | 107T840 | tr_TR |
dc.rights | info:eu-repo/semantics/closedAccess | en_US |
dc.subject | Dipolar cycloaddition | en_US |
dc.subject | Cyclic nitrones | en_US |
dc.subject | 4-Isoxazolines | en_US |
dc.subject | Ylides | en_US |
dc.subject | Rearrangement | en_US |
dc.subject | NHCs | en_US |
dc.subject | Ag(I) metallated imidazolium ylides | en_US |
dc.subject | Imıdazoline 3-oxides | en_US |
dc.subject | Diastereoselective addition | en_US |
dc.subject | 1,3-dipolar cycloaddition | en_US |
dc.subject | Regio | en_US |
dc.subject | Reactivity | en_US |
dc.subject | Complexes | en_US |
dc.subject | Chemistry | en_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 dicarboxylate | en_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 dicarboxylate | en_US |
dc.subject.emtree | 1 (3,4 dimethoxyphenyl) 4 phenyl 1h imidazole; 1 (3,4 dimethoxyphenyl) 4 phenyl 2,5 dihydro 1h imidazole 3 oxide | en_US |
dc.subject.emtree | 1 (4 bromophenyl) 4 phenyl 1h imidazole | en_US |
dc.subject.emtree | 1 (4 chlorophenyl) 4 phenyl 1h imidazole | en_US |
dc.subject.emtree | 1 (4 methoxyphenyl) 2,4 diphenyl 1h imidazole | en_US |
dc.subject.emtree | 1 (4 methoxyphenyl) 4 phenyl 1h imidazole | en_US |
dc.subject.emtree | 1,4 diphenyl 1h imidazole | en_US |
dc.subject.emtree | 2 (3 nitrophenyl) 5 phenyl 3 p tolyl 3h imidazol 1 ium 1 (1,2 bis methoxycarbonyl 2 oxoethanide) | en_US |
dc.subject.emtree | 2 (3,4 dimethoxyphenyl) 5 phenyl 3 p tolyl 3h imidazol 1 ium 1 (1,2 bis methoxycarbonyl 2 oxoethanide) | en_US |
dc.subject.emtree | 2 (4 chlorophenyl) 5 phenyl 3 p tolyl 3h imidazol 1 ium 1 (1,2 bis methoxycarbonyl 2 oxoethanide) | en_US |
dc.subject.emtree | 2,4 diphenyl 1 p tolyl 1h imidazole | en_US |
dc.subject.emtree | 3 (3,4 dimethoxyphenyl) 5 phenyl 3h imidazol 1 ium 1 (1,2 bis methoxycarbonyl 2 oxoethanide) | en_US |
dc.subject.emtree | 3 (4 bromophenyl) 5 phenyl 3h imidazol 1 ium 1 (1,2 bismethoxycarbonyl 2 oxoethanide) | en_US |
dc.subject.emtree | 3 (4 chlorophenyl) 5 phenyl 3h imidazol 1 ium 1 (1,2 bismethoxycarbonyl 2 oxoethanide) | en_US |
dc.subject.emtree | 3 (4 methoxyphenyl) 2,5 diphenyl 3h imidazol 1 ium 1 (1,2 bis methoxycarbonyl 2 oxoethanide) | en_US |
dc.subject.emtree | 3 (4 methoxyphenyl) 5 phenyl 3h imidazol 1 ium 1 (1,2-bis methoxycarbonyl 2 oxoethanide) | en_US |
dc.subject.emtree | 3 (p tolyl) 2 (4 methoxyphenyl) 5 phenyl 3h imidazol 1 ium 1 (1,2 bis methoxycarbonyl 2 oxoethanide) | en_US |
dc.subject.emtree | 3 (p tolyl) 2,5 diphenyl 3h imidazol 1 ium 1 (1,2 bis methoxycarbonyl 2 oxoethanide) | en_US |
dc.subject.emtree | 3,4 dihydro 2h imidazol 1 ium 1 (1,2 bis methoxycarbonyl 2 oxo ethanide) | en_US |
dc.subject.emtree | 3,5 diphenyl 3h imidazol 1 ium 1 (1,2 bis methoxycarbonyl 2 oxoethanide) | en_US |
dc.subject.emtree | 3h imidazol 1 ium 1 (1,2 bis methoxycarbonyl 2 oxo ethanide) | en_US |
dc.subject.emtree | 4 phenyl 1 p tolyl 1h imidazole; 5 phenyl 3 p methoxyphenyl 3h imidazol 1 ium 1 [(1 methoxycarbonyl) 2 menthyloxycarbonyl] 2 oxoethanide | en_US |
dc.subject.emtree | 5 phenyl 3 p tolyl 3h imidazol 1 ium 1 (1,2 bis methoxycarbonyl 2 oxoethanide) | en_US |
dc.subject.emtree | 5 phenyl 3 p tolyl 3h imidazol 1 ium 1 [(1 methoxycarbonyl) 2 menthyloxycarbonyl] 2 oxoethanide | en_US |
dc.subject.emtree | Imidazole derivative | en_US |
dc.subject.emtree | Isoxazoline derivative | en_US |
dc.subject.emtree | Toluene | en_US |
dc.subject.emtree | Unclassified drug | en_US |
dc.subject.emtree | Article | en_US |
dc.subject.emtree | Cycloaddition | en_US |
dc.subject.emtree | Drug synthesis | en_US |
dc.subject.emtree | Priority journal | en_US |
dc.subject.emtree | Reaction analysis | en_US |
dc.subject.emtree | Thermal analysis | en_US |
dc.subject.scopus | Nitrones; Cycloaddition Reactions; Hydroxylamines | en_US |
dc.subject.wos | Chemistry, organic | en_US |
dc.title | Thermal rearrangements of tetrahydroimidazo[1,5-b]isoxazole-2,3-dicarboxylates. Synthesis of 3H-imidazol-1-ium ylides and their silver derivatives | en_US |
dc.type | Article | |
dc.wos.quartile | Q1 | en_US |
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