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 dokumentuApstrakt
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 cyclizationIzvor:
Tetrahedron, 2017, 73, 44, 6268-6274Projekti:
DOI: 10.1016/j.tet.2017.09.014
ISSN: 0040-4020