1. Synthesis of novel 4-ferrocenyl-1,2,3,4-tetrahydroquinolines and 4-ferrocenylquinolines via α-ferrocenyl carbenium ions as key intermediates
- Author
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Dragana Stevanović, Mirjana Vukićević, Matthias D'hooghe, Aleksandra Minić, Rastko D. Vukićević, Niko S. Radulović, and Goran A. Bogdanović
- Subjects
STRUCTURAL-CHARACTERIZATION ,ANTIMALARIAL ,DDQ ,010402 general chemistry ,01 natural sciences ,Biochemistry ,Medicinal chemistry ,Ion ,ARYL KETONES ,ELECTROORGANIC REACTIONS ,chemistry.chemical_compound ,Acetic acid ,Carbenium ion ,RECENT PROGRESS ,Drug Discovery ,Organic chemistry ,010405 organic chemistry ,Anodic oxidation ,Aryl ,Tetrahydroquinolines ,Organic Chemistry ,Intramolecular cyclization ,DDQ aromatization ,IN-VITRO ,alpha-Ferrocenyl carbenium ion ,BENZYLIC OXIDATION ,0104 chemical sciences ,Chemistry ,CONVENIENT SYNTHESIS ,chemistry ,Quinolines ,ANODIC-OXIDATION - 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.
- Published
- 2017