Regioselective bromination: Synthesis of brominated methoxyquinolines

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dc.contributor.authorÇakmak, Osman
dc.contributor.authorÖkten, Salih
dc.date.accessioned2020-06-25T18:22:43Z
dc.date.available2020-06-25T18:22:43Z
dc.date.issued2017
dc.departmentKırıkkale Üniversitesi
dc.descriptionOkten, Salih/0000-0001-9656-1803
dc.description.abstractSimple synthetic methods are described for the synthesis of valuable polyfunctional brominated methoxyquinolines 10-13, 20-21, and 24-25. Three regioselective routes are described for convenient preparation of brominated methoxyquinolines at the C-2, C-3, and C-5 positions with consecutive reaction steps under mild reaction conditions using molecular bromine. While bromination of 6-bromo-8methoxy-1,2,3,4-tetrahydroquinoline (8) selectively gave 3,6-dibromo-8-methoxyquinoline (10) and 3,5,6-tribromo-8-methoxyquinoline (11), the reaction of 6,8-dimethoxy-1,2,3,4-tetrahydroquinoline (9) resulted in the formation of 3-bromo-6,8-dimethoxyqinoline (12) and tribromide 13. On the other hand, direct bromination of 6-methoxy- 17 and 6,8-dimethoxyquinoline (19) gave 5-bromo derivatives 20 and 21. However, the reaction 3,6-dimethoxyquinoline (8) resulted in dibromination to form 2,5dibromoquinoline (24). This process selectively led to functionalization of the quinoline ring at both the C-2 and C-5 positions. (C)2017 Elsevier Ltd. All rights reserved.en_US
dc.description.sponsorshipScientific and Technological Research Council of Turkey (TUBITAK)Turkiye Bilimsel ve Teknolojik Arastirma Kurumu (TUBITAK) [112T394]en_US
dc.description.sponsorshipThe study was supported by grants from the Scientific and Technological Research Council of Turkey (TUBITAK, Project number: 112T394).en_US
dc.identifier.citationclosedAccessen_US
dc.identifier.doi10.1016/j.tet.2017.07.044
dc.identifier.endpage5396en_US
dc.identifier.issn0040-4020
dc.identifier.issue36en_US
dc.identifier.scopus2-s2.0-85026428774
dc.identifier.scopusqualityQ3
dc.identifier.startpage5389en_US
dc.identifier.urihttps://doi.org/10.1016/j.tet.2017.07.044
dc.identifier.urihttps://hdl.handle.net/20.500.12587/6876
dc.identifier.volume73en_US
dc.identifier.wosWOS:000408179400008
dc.identifier.wosqualityQ2
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.language.isoen
dc.publisherPergamon-Elsevier Science Ltden_US
dc.relation.ispartofTetrahedron
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/closedAccessen_US
dc.subjectQuinolineen_US
dc.subject1,2,3,4-Tetrahydroquinolineen_US
dc.subjectBromo quinolineen_US
dc.subjectMethoxy quinolineen_US
dc.subjectBromination of methoxy quinolineen_US
dc.subjectMultifunctionalization of quinolineen_US
dc.subjectRegioselective brominationen_US
dc.subjectMolecular bromineen_US
dc.titleRegioselective bromination: Synthesis of brominated methoxyquinolinesen_US
dc.typeArticle

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