Convenient synthesis of disubstituted tacrine derivatives via electrophilic and copper induced reactions

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dc.contributor.authorEkiz, Makbule
dc.contributor.authorTutar, Ahmet
dc.contributor.authorOkten, Salih
dc.date.accessioned2020-06-25T18:16:17Z
dc.date.available2020-06-25T18:16:17Z
dc.date.issued2016
dc.departmentKırıkkale Üniversitesi
dc.descriptionOkten, Salih/0000-0001-9656-1803; Tutar, Ahmet/0000-0001-5524-8001
dc.description.abstractThe bromination of 2-aminobenzonitrile (2) with molecular bromine (2 equiv) furnished 2-amino-3,5-dibromobenzonitrile (7) in 98% yield. One-pot syntheses are described for dibromotacrine derivatives (6,14-18) utilizing Friedlander reactions. A convenient route is described for disubstituted derivatives of tacrines from dibromotacrine 6 and 15 by various substitution reactions. Several disubstituted tacrines were synthesized by treatment of dibromo 6 and 15 derivatives with n-BuLi followed by trapping with an electrophile [Si(Me)(3)Cl, S-2(Me)(2)]. Both were converted to the corresponding cyano derivatives (21-23) via copper-assisted nucleophilic substitution reactions in moderate yields (30%, 50%, and 60%, respectively). Copper-induced nucleophilic substitution of dibromide 15 with NaOMe afforded mono methoxide 31 in 25% yield. (C) 2016 Elsevier Ltd. All rights reserved.en_US
dc.description.sponsorshipSakarya University Research FundSakarya University [2014-02-04-008]en_US
dc.description.sponsorshipThis study was supported by grants from the Sakarya University Research Fund (Project number: 2014-02-04-008).en_US
dc.identifier.citationclosedAccessen_US
dc.identifier.doi10.1016/j.tet.2016.07.012
dc.identifier.endpage5330en_US
dc.identifier.issn0040-4020
dc.identifier.issue35en_US
dc.identifier.scopus2-s2.0-84979949601
dc.identifier.scopusqualityQ3
dc.identifier.startpage5323en_US
dc.identifier.urihttps://doi.org/10.1016/j.tet.2016.07.012
dc.identifier.urihttps://hdl.handle.net/20.500.12587/6483
dc.identifier.volume72en_US
dc.identifier.wosWOS:000381530900009
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.subjectTacrineen_US
dc.subjectBromotacrineen_US
dc.subjectCyanotacrineen_US
dc.subjectLithium-bromine exchangeen_US
dc.subjectThiomethyltacrineen_US
dc.subjectMethoxytacrineen_US
dc.titleConvenient synthesis of disubstituted tacrine derivatives via electrophilic and copper induced reactionsen_US
dc.typeArticle

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