Issue 12, 2018

New 2-(aryl/heteroaryl)-6-(morpholin-4-yl/pyrrolidin-1-yl)-(4-trifluoromethyl)quinolines: synthesis via Buchwald–Hartwig amination, photophysics, and biomolecular binding properties

Abstract

This work reports a successful synthesis of two new series of 2-(aryl/heteroaryl)-6-(morpholin-4-yl/pyrrolidin-1-yl)-(4-trifluoromethyl)quinolines via the Buchwald–Hartwig amination, at 60–88% yields, starting from 2-(aryl/heteroaryl)-6-bromo-4-trifluoromethyl-quinolines and heteroarylamines (morpholine and pyrrolidine). The 6-bromoquinoline precursors were obtained from an easy intramolecular cyclization reaction of (Z)-4-((4-bromophenyl)amino)-1,1,1-trifluoro-but-3-en-2-ones, which were previously prepared through the reaction of 4-methoxy-(aryl/heteroaryl)-1,1,1-trifluoroalk-3-en-2-ones with 4-bromoaniline. Photophysical analyses indicated intraligand and charge-transfer type transitions, in agreement with the aromatic structures of the heterocycle moieties. In the case of ct-DNA titrations (via the absorption and emission method), morpholinyl- and pyrrolydinyl-substituted quinolines had strong interactions with ct-DNA, which could be attributed to π-stacking and/or hydrogen-bonding interactions.

Graphical abstract: New 2-(aryl/heteroaryl)-6-(morpholin-4-yl/pyrrolidin-1-yl)-(4-trifluoromethyl)quinolines: synthesis via Buchwald–Hartwig amination, photophysics, and biomolecular binding properties

Supplementary files

Article information

Article type
Paper
Submitted
07 Mar 2018
Accepted
10 May 2018
First published
11 May 2018

New J. Chem., 2018,42, 10024-10035

New 2-(aryl/heteroaryl)-6-(morpholin-4-yl/pyrrolidin-1-yl)-(4-trifluoromethyl)quinolines: synthesis via Buchwald–Hartwig amination, photophysics, and biomolecular binding properties

H. G. Bonacorso, M. B. Rodrigues, B. A. Iglesias, C. H. da Silveira, S. C. Feitosa, W. C. Rosa, M. A. P. Martins, C. P. Frizzo and N. Zanatta, New J. Chem., 2018, 42, 10024 DOI: 10.1039/C8NJ01120F

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