NOVEL 4-FERROCENYL-8-(PHENYLTHIO)-1,2,3,4-TETRAHYDROQUINOLINE: DESIGN, SYNTHESIS AND SPECTRAL CHARACTERIZATION

Authors

Aleksandra Minić

Faculty of Technical Sciences, University of Priština, Kneza Miloša 7, 38220 Kosovska Mitrovica, Serbia

Jovana Bugarinović

Faculty of Science, University of Kragujevac, Kragujevac, Serbia

Marko Pešić

Faculty of Science, University of Kragujevac, Radoja Domanovića 12, 34000 Kragujevac, Serbia

Danijela Ilić Komatina

Faculty of Technical Sciences, University of Priština in Kosovska Mitrovica, Kosovska Mitrovica, Serbia

DOI 10.5937/univtho9-20839 Original page Cite this article

Keywords

Tetrahydroquinoline ring, Ferrocene, Intramolecular cyclization, α-Ferrocenyl carbocation, Spectral characterization

Abstract

Herein, we report design, synthesis and spectral characterization of novel 4-ferrocenyl-8-(phenylthio)-1,2,3,4-tetrahydroquinoline. Desired synthesis was achieved in three reaction steps, with a good overall yield (67%). First step included aza-Michael addition of 2-(phenylthio)aniline to 1-ferrocenylpropenone, subsequently, the obtained ketone was smoothly reduced to the corresponding 1,3-amino alcohol. The final step was an intramolecular cyclization prompted by acetic acid, proceeding via corresponding α-ferrocenyl carbocation. The synthesized compounds have been isolated pure, and their structure have been undoubtedly confirmed by standard spectral techniques (1H NMR, 13C NMR, IR and elemental analyses).

Issue

Vol. 9 No. 1 (2019)

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