Synthesis of stable azomethineylides by the rearrangement of 1,3-dipolar cycloadducts of 3,4-dihydroisoquinoline-2-oxides with DMAD
dc.contributor.buuauthor | Coşkun, Necdet | |
dc.contributor.buuauthor | Tunçman, Selen | |
dc.contributor.department | Uludağ Üniversitesi/Fen-Edebiyat Fakültesi/Kimya Bölümü. | tr_TR |
dc.contributor.scopusid | 7004177880 | tr_TR |
dc.contributor.scopusid | 11540067400 | tr_TR |
dc.date.accessioned | 2022-01-31T10:40:40Z | |
dc.date.available | 2022-01-31T10:40:40Z | |
dc.date.issued | 2006-02-13 | |
dc.description.abstract | 1-Aryl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolines were prepared according to a one-pot procedure involving the reaction of 2-(3,4-dimethoxyl)-ethylamine with aromatic aldehydes in TFA at reflux. The tetrahydroisoquinolines were treated with H2O2-WO42- in methanol at room temperature to give the corresponding 3,4-dihydroisoquinoline-2-oxides. Treatment of these cyclic nitrones with DMAD in toluene at room temperature gave the corresponding isoxazolo[3,2-a]isoquinolines. These compounds were heated in toluene at reflux to give the corresponding ylides in high yields (Method A). The effect of the substituents on the rate of the rearrangement of such compounds prompted us to discuss a new mechanism involving consecutive C-C bond heterolysis and 1,3-sigmatropic shift. A one-pot reaction involving the treatment of the nitrones with equimolar amounts of DMAD in refluxing toluene also gave the ylides (Method B). The structures of the prepared compound,, were elucidated by spectral means and elemental analyses. | en_US |
dc.identifier.citation | Coşkun, N. ve Tunçman, S. (2006). ''Synthesis of stable azomethineylides by the rearrangement of 1,3-dipolar cycloadducts of 3,4-dihydroisoquinoline-2-oxides with DMAD''. Tetrahedron, 62(7), 1345-1350. | en_US |
dc.identifier.endpage | 1350 | tr_TR |
dc.identifier.issn | 0040-4020 | |
dc.identifier.issue | 7 | tr_TR |
dc.identifier.scopus | 2-s2.0-30844447445 | tr_TR |
dc.identifier.startpage | 1345 | tr_TR |
dc.identifier.uri | https://doi.org/10.1016/j.tet.2005.11.040 | |
dc.identifier.uri | https://www.sciencedirect.com/science/article/pii/S0040402005020429 | |
dc.identifier.uri | http://hdl.handle.net/11452/24321 | |
dc.identifier.volume | 62 | tr_TR |
dc.identifier.wos | 000235123900002 | 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.rights | info:eu-repo/semantics/closedAccess | en_US |
dc.subject | Chemistry | en_US |
dc.subject | Heterocycles | en_US |
dc.subject | Synthesis | en_US |
dc.subject | Dipolar cycloaddition | en_US |
dc.subject | DMAD | en_US |
dc.subject | Alkyne | en_US |
dc.subject | 4-Isoxazoline rearrangement mechanism | en_US |
dc.subject | Stable azomethine ylide | en_US |
dc.subject | Isoxazoloisoquinoline | en_US |
dc.subject | Rearrangement | en_US |
dc.subject | Oxidation with H2O2–tungstate | en_US |
dc.subject | Pictet–Spengler | en_US |
dc.subject | Isoquinoline | en_US |
dc.subject | 3,4-Dihydroisoquinoline-2-oxide | en_US |
dc.subject | THI | en_US |
dc.subject | 1-Aryl-1,2,3,4-tetrahydroisoquinoline | en_US |
dc.subject | Nitrones | en_US |
dc.subject | Regio | en_US |
dc.subject | N-oxides | en_US |
dc.subject | Aryl isocyanates | en_US |
dc.subject | Organic-synthesis | en_US |
dc.subject | Cloaddition reactions | en_US |
dc.subject | Diastereoselective additioncy | en_US |
dc.subject | Imidazoline 3-oxides | en_US |
dc.subject | Ring-opening reactions | en_US |
dc.subject.emtree | 1 (3,4 dimethoxyphenyl) 6,7 dimethoxy 1,2,3,4 tetrahydroisoquinoline | en_US |
dc.subject.emtree | 1 (4 chlorophenyl) 6,7 dimethoxy 1,2,3,4 tetrahydroisoquinoline | en_US |
dc.subject.emtree | 1 benzo[1,3]dioxol 5 yl 6,7 dimethoxy 1,2,3,4 tetrahydroisoquinoline | en_US |
dc.subject.emtree | 6,7 dimethoxy 1 (3 nitrophenyl) 1,2,3,4 tetrahydroisoquinoline | en_US |
dc.subject.emtree | 6,7 dimethoxy 1 phenyl 1,2,3,4 tetrahydroisoquinoline | en_US |
dc.subject.emtree | Azomethine ylide | en_US |
dc.subject.emtree | Hydrogen peroxide | en_US |
dc.subject.emtree | Isoquinoline derivative | en_US |
dc.subject.emtree | Methanol | en_US |
dc.subject.emtree | Nitrone derivative | en_US |
dc.subject.emtree | Toluene | en_US |
dc.subject.emtree | Unclassified drug | en_US |
dc.subject.emtree | Synthesis | en_US |
dc.subject.emtree | Spectroscopy | en_US |
dc.subject.emtree | Room temperature | en_US |
dc.subject.emtree | Reaction analysis | en_US |
dc.subject.emtree | Priority journal | en_US |
dc.subject.emtree | Oxidation | en_US |
dc.subject.emtree | Cycloaddition | en_US |
dc.subject.emtree | Article | en_US |
dc.subject.scopus | Nitrones; Cycloaddition Reactions; Hydroxylamines | en_US |
dc.subject.wos | Chemistry, organic | en_US |
dc.title | Synthesis of stable azomethineylides by the rearrangement of 1,3-dipolar cycloadducts of 3,4-dihydroisoquinoline-2-oxides with DMAD | en_US |
dc.type | Article | |
dc.wos.quartile | Q2 | en_US |
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