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Synthesis of novel 4-ferrocenyl-1,2,3,4-tetrahydroquinolines and 4-ferrocenylquinolines via alpha-ferrocenyl carbenium ions as key intermediates
dc.creator | Minić, Aleksandra | |
dc.creator | Stevanović, Dragana D. | |
dc.creator | Vukićević, Mirjana | |
dc.creator | Bogdanović, Goran A. | |
dc.creator | D'hooghe, Matthias | |
dc.creator | Radulović, Niko S. | |
dc.creator | Vukićević, Rastko D. | |
dc.date.accessioned | 2018-03-01T17:56:59Z | |
dc.date.available | 2018-03-01T17:56:59Z | |
dc.date.issued | 2017 | |
dc.identifier.issn | 0040-4020 | |
dc.identifier.uri | https://vinar.vin.bg.ac.rs/handle/123456789/1797 | |
dc.description.abstract | A series of novel 4-ferrocenyl-1,2,3,4-tetrahydroquinolines were synthesized in high-to-excellent yields (up to 99%) starting from the corresponding ferrocenoylethyl aryl amines. These Mannich bases were reduced (NaBH4) to the corresponding 3-(arylamino)-1-ferrocenylpropan-1-ols and submitted to an intramolecular cyclization prompted by acetic acid, proceeding via the corresponding alpha-ferrocenyl carbenium ion intermediates. Subsequently, the obtained tetrahydroquinolines were smoothly oxidized (aromatized) by means of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) to provide the corresponding 4-ferrocenylquinolines (up to 93%). (C) 2017 Elsevier Ltd. All rights reserved. | en |
dc.relation | info:eu-repo/grantAgreement/MESTD/Basic Research (BR or ON)/172034/RS// | |
dc.rights | restrictedAccess | en |
dc.source | Tetrahedron | en |
dc.subject | alpha-Ferrocenyl carbenium ion | en |
dc.subject | Quinolines | en |
dc.subject | Tetrahydroquinolines | en |
dc.subject | DDQ aromatization | en |
dc.subject | Intramolecular cyclization | en |
dc.title | Synthesis of novel 4-ferrocenyl-1,2,3,4-tetrahydroquinolines and 4-ferrocenylquinolines via alpha-ferrocenyl carbenium ions as key intermediates | en |
dc.type | article | en |
dc.rights.license | ARR | |
dcterms.abstract | Д'хоогхе, Маттхиас; Богдановић Горан; Вукицевиц, Растко Д.; Миниц, Aлександра; Стевановиц, Драгана; Радуловиц, Нико С.; Вукицевиц, Мирјана; | |
dc.citation.volume | 73 | |
dc.citation.issue | 44 | |
dc.citation.spage | 6268 | |
dc.citation.epage | 6274 | |
dc.identifier.wos | 000413798200004 | |
dc.identifier.doi | 10.1016/j.tet.2017.09.014 | |
dc.citation.rank | M22 | |
dc.type.version | publishedVersion | |
dc.identifier.scopus | 2-s2.0-85029782580 |