1. Chemoselective synthesis of isolated and fused fluorenones and their photophysical and antiviral properties
- Author
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Ismail Althagafi, Ranjay Shaw, Chanda Sinha, Shally, Cheng-Run Tang, Amit Kumar, Rahul Panwar, Yong-Tang Zheng, and Ramendra Pratap
- Subjects
Fluorenes ,010405 organic chemistry ,Organic Chemistry ,Chemistry Techniques, Synthetic ,010402 general chemistry ,Lithium aluminium hydride ,Ring (chemistry) ,01 natural sciences ,Biochemistry ,Fluorescence ,Medicinal chemistry ,Antiviral Agents ,0104 chemical sciences ,Solvent ,chemistry.chemical_compound ,Spectrometry, Fluorescence ,chemistry ,Terphenyl ,Yield (chemistry) ,Nitriles ,Amine gas treating ,Reactivity (chemistry) ,Physical and Theoretical Chemistry - Abstract
Highly functionalized fluorenones were synthesized by an intramolecular cyclization of 2''-halo-[1,1':3',1''-terphenyl]-4'-carbonitriles in the presence of n-butyllithium or lithium aluminium hydride. The precursor was synthesized by ring transformation of 2-oxo-6-aryl/heteroaryl-4-(sec.amino)-2H-pyran-3-carbonitriles or 2-oxobenzo[h]chromenes with o-bromo/chloro/fluoro-acetophenone under basic conditions in moderate yield. We performed the control experiment to understand the proposed mechanism and found that the presence of a secondary amine in the starting material directs the reactivity. The photophysical properties of 3-methoxy-7-(piperidin-1-yl)-5H-indeno[2,1-b]phenanthren-8(6H)-one was explored and solvent dependent emission was observed. These compounds were also tested against HIV-1 and low to moderate activity was observed.
- Published
- 2018