Synthesis of novel 4-ferrocenyl-1,2,3,4-tetrahydroquinolines and 4-ferrocenylquinolines via alpha-ferrocenyl carbenium ions as key intermediates
Само за регистроване кориснике
2017
Аутори
Minić, Aleksandra
Stevanović, Dragana D.

Vukicevic, Mirjana
Bogdanović, Goran A.

D'hooghe, Matthias
Radulovic, Niko S.

Vukicevic, Rastko D.
Чланак у часопису
Метаподаци
Приказ свих података о документуАпстракт
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.
Кључне речи:
alpha-Ferrocenyl carbenium ion / Quinolines / Tetrahydroquinolines / DDQ aromatization / Intramolecular cyclizationИзвор:
Tetrahedron, 2017, 73, 44, 6268-6274Пројекти:
DOI: 10.1016/j.tet.2017.09.014
ISSN: 0040-4020