Novel 4-ferrocenyl-8-(phenylthio)-1,2,3,4-tetrahydroquinoline: Design, synthesis and spectral characterization

• Main Authors: Minić Aleksandra, Bugarinović Jovana, Pešić Marko, Ilić-Komatina Danijela
• Format: Article
• Language: English
• Published: University of Priština - Faculty of Natural Science and Mathematics, Kosovska Mitrovica 2019-01-01
• Series: The University Thought: Publication in Natural Sciences
• Subjects: Tetrahydroquinoline ring; Ferrocene; Intramolecular cyclization; α-Ferrocenyl carbocation; Spectral characterization
• Online Access: https://scindeks-clanci.ceon.rs/data/pdf/1450-7226/2019/1450-72261901038M.pdf

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).