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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

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2017
Authors
Minić, Aleksandra
Stevanović, Dragana D.
Vukicevic, Mirjana
Bogdanović, Goran A.
D'hooghe, Matthias
Radulovic, Niko S.
Vukicevic, Rastko D.
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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.
Keywords:
alpha-Ferrocenyl carbenium ion / Quinolines / Tetrahydroquinolines / DDQ aromatization / Intramolecular cyclization
Source:
Tetrahedron, 2017, 73, 44, 6268-6274
Projects:
  • Novel Electrochemical and Chemical Methods in Synthesis of Organic Compounds of Interest for Medicine and Material Chemistry (RS-172034)

DOI: 10.1016/j.tet.2017.09.014

ISSN: 0040-4020 (print)

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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Vinča

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