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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

Samo za registrovane korisnike
2017
Autori
Minić, Aleksandra
Stevanović, Dragana D.
Vukicevic, Mirjana
Bogdanović, Goran A.
D'hooghe, Matthias
Radulovic, Niko S.
Vukicevic, Rastko D.
Članak u časopisu
Metapodaci
Prikaz svih podataka o dokumentu
Apstrakt
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.
Ključne reči:
alpha-Ferrocenyl carbenium ion / Quinolines / Tetrahydroquinolines / DDQ aromatization / Intramolecular cyclization
Izvor:
Tetrahedron, 2017, 73, 44, 6268-6274
Projekti:
  • Nove elektrohemijske i hemijske metode u sintezi organskih jedinjenja od interesa za medicinu i hemiju materijala (RS-172034)

DOI: 10.1016/j.tet.2017.09.014

ISSN: 0040-4020

WoS: 000413798200004

Scopus: 2-s2.0-85029782580
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URI
http://vinar.vin.bg.ac.rs/handle/123456789/1797
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Institucija
Vinča

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