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.
TY - JOUR
AU - Minić, Aleksandra
AU - Stevanović, Dragana D.
AU - Vukicevic, Mirjana
AU - Bogdanović, Goran A.
AU - D'hooghe, Matthias
AU - Radulovic, Niko S.
AU - Vukicevic, Rastko D.
PY - 2017
UR - http://vinar.vin.bg.ac.rs/handle/123456789/1797
AB - 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.
T2 - Tetrahedron
T1 - Synthesis of novel 4-ferrocenyl-1,2,3,4-tetrahydroquinolines and 4-ferrocenylquinolines via alpha-ferrocenyl carbenium ions as key intermediates
VL - 73
IS - 44
SP - 6268
EP - 6274
DO - 10.1016/j.tet.2017.09.014
ER -
@article{
author = "Minić, Aleksandra and Stevanović, Dragana D. and Vukicevic, Mirjana and Bogdanović, Goran A. and D'hooghe, Matthias and Radulovic, Niko S. and Vukicevic, Rastko D.",
year = "2017",
url = "http://vinar.vin.bg.ac.rs/handle/123456789/1797",
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.",
journal = "Tetrahedron",
title = "Synthesis of novel 4-ferrocenyl-1,2,3,4-tetrahydroquinolines and 4-ferrocenylquinolines via alpha-ferrocenyl carbenium ions as key intermediates",
volume = "73",
number = "44",
pages = "6268-6274",
doi = "10.1016/j.tet.2017.09.014"
}
Minić A, Stevanović DD, Vukicevic M, Bogdanović GA, D'hooghe M, Radulovic NS, Vukicevic RD. Synthesis of novel 4-ferrocenyl-1,2,3,4-tetrahydroquinolines and 4-ferrocenylquinolines via alpha-ferrocenyl carbenium ions as key intermediates. Tetrahedron. 2017;73(44):6268-6274
Minić, A., Stevanović, D. D., Vukicevic, M., Bogdanović, G. A., D'hooghe, M., Radulovic, N. S.,& Vukicevic, R. D. (2017). Synthesis of novel 4-ferrocenyl-1,2,3,4-tetrahydroquinolines and 4-ferrocenylquinolines via alpha-ferrocenyl carbenium ions as key intermediates.
Tetrahedron, 73(44), 6268-6274.
https://doi.org/10.1016/j.tet.2017.09.014
Minić Aleksandra, Stevanović Dragana D., Vukicevic Mirjana, Bogdanović Goran A., D'hooghe Matthias, Radulovic Niko S., Vukicevic Rastko D., "Synthesis of novel 4-ferrocenyl-1,2,3,4-tetrahydroquinolines and 4-ferrocenylquinolines via alpha-ferrocenyl carbenium ions as key intermediates" 73, no. 44 (2017):6268-6274,
https://doi.org/10.1016/j.tet.2017.09.014 .
