Synthesis of novel 4-ferrocenyl-1,2,3,4-tetrahydroquinolines and 4-ferrocenylquinolines via alpha-ferrocenyl carbenium ions as key intermediates
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2017
Authors
Minić, AleksandraStevanović, Dragana D.
Vukićević, Mirjana
Bogdanović, Goran A.
D'hooghe, Matthias
Radulović, Niko S.
Vukićević, Rastko D.
Article (Published version)
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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.
Keywords:
alpha-Ferrocenyl carbenium ion / Quinolines / Tetrahydroquinolines / DDQ aromatization / Intramolecular cyclizationSource:
Tetrahedron, 2017, 73, 44, 6268-6274Funding / projects:
- Novel Electrochemical and Chemical Methods in Synthesis of Organic Compounds of Interest for Medicine and Material Chemistry (RS-MESTD-Basic Research (BR or ON)-172034)
DOI: 10.1016/j.tet.2017.09.014
ISSN: 0040-4020
WoS: 000413798200004
Scopus: 2-s2.0-85029782580
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VinčaTY - JOUR AU - Minić, Aleksandra AU - Stevanović, Dragana D. AU - Vukićević, Mirjana AU - Bogdanović, Goran A. AU - D'hooghe, Matthias AU - Radulović, Niko S. AU - Vukićević, Rastko D. PY - 2017 UR - https://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 Vukićević, Mirjana and Bogdanović, Goran A. and D'hooghe, Matthias and Radulović, Niko S. and Vukićević, Rastko D.", year = "2017", 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, D. D., Vukićević, M., Bogdanović, G. A., D'hooghe, M., Radulović, N. S.,& Vukićević, R. D.. (2017). Synthesis of novel 4-ferrocenyl-1,2,3,4-tetrahydroquinolines and 4-ferrocenylquinolines via alpha-ferrocenyl carbenium ions as key intermediates. in Tetrahedron, 73(44), 6268-6274. https://doi.org/10.1016/j.tet.2017.09.014
Minić A, Stevanović DD, Vukićević M, Bogdanović GA, D'hooghe M, Radulović NS, Vukićević RD. Synthesis of novel 4-ferrocenyl-1,2,3,4-tetrahydroquinolines and 4-ferrocenylquinolines via alpha-ferrocenyl carbenium ions as key intermediates. in Tetrahedron. 2017;73(44):6268-6274. doi:10.1016/j.tet.2017.09.014 .
Minić, Aleksandra, Stevanović, Dragana D., Vukićević, Mirjana, Bogdanović, Goran A., D'hooghe, Matthias, Radulović, Niko S., Vukićević, Rastko D., "Synthesis of novel 4-ferrocenyl-1,2,3,4-tetrahydroquinolines and 4-ferrocenylquinolines via alpha-ferrocenyl carbenium ions as key intermediates" in Tetrahedron, 73, no. 44 (2017):6268-6274, https://doi.org/10.1016/j.tet.2017.09.014 . .