Journal
NEW JOURNAL OF CHEMISTRY
Volume 43, Issue 31, Pages 12375-12384Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c9nj01681c
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Funding
- Conselho Nacional de Desenvolvimento Cientifico e Tecnologico (CNPq) [402.075/2016-1]
- Fundacao de Amparo a Pesquisa do Estado do Rio Grande do Sul (FAPERGS) [17/2551-0001275-5, 18/2551-0000562-2]
- National Institute of Science and Technology on Tuberculosis (Decit/SCTIE/MS-MCT-CNPq-FNDTC-CAPES-FAPERGS) [421703/2017-2]
- Coordenacao de Aperfeicoamento de Pessoal de Nivel Superior (CAPES) [88887.197556/2018-00]
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The synthesis and structural elucidation of a new series of six 6-amino-2-alkyl(aryl/heteroaryl)-4-(trifluoromethyl) quinolines are reported, yielding 22 to 87% isolated products. This was achieved through a regioselective intramolecular cyclization reaction of novel (Z)-4-((4-aminophenyl)amino)-1,1,1-trifluoro-but-3-en-2-ones in an acidic solvent-free medium, in which alkyl/aryl/heteroaryl = methyl, phenyl, 4-MeC6H4, 4-FC6H4, 4-NO2C6H4, and 2-furyl. The novel compounds were fully characterized by H-1-, C-13- and F-19-NMR spectroscopy, GC-MS and single-crystal X-ray diffraction. In addition, the preliminary investigation of photophysical properties of the 6-aminoquinolines (UV-Vis, fluorescence, quantum yield calculations, Stokes shifts, and TD-DFT analysis) and inhibitory activity against M. tuberculosis H37Rv strain was also presented. Thermal analyses were carried out to assess their properties as new materials.
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