Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
5211850 | Tetrahedron | 2017 | 7 Pages |
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 α-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%).
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Related Topics
Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Aleksandra MiniÄ, Dragana StevanoviÄ, Mirjana VukiÄeviÄ, Goran A. BogdanoviÄ, Matthias D'hooghe, Niko S. RaduloviÄ, Rastko D. VukiÄeviÄ,