Jump to main content
Jump to site search
Access to RSC content Close the message box

Continue to access RSC content when you are not at your institution. Follow our step-by-step guide.


Issue 40, 2018
Previous Article Next Article

Chemoselective synthesis of isolated and fused fluorenones and their photophysical and antiviral properties

Author affiliations

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.

Graphical abstract: Chemoselective synthesis of isolated and fused fluorenones and their photophysical and antiviral properties

Back to tab navigation

Supplementary files

Article information


Submitted
19 Jul 2018
Accepted
18 Sep 2018
First published
19 Sep 2018

Org. Biomol. Chem., 2018,16, 7477-7487
Article type
Paper

Chemoselective synthesis of isolated and fused fluorenones and their photophysical and antiviral properties

I. Althagafi, R. Shaw, C. Tang, R. Panwar, Shally, C. Sinha, A. Kumar, Y. Zheng and R. Pratap, Org. Biomol. Chem., 2018, 16, 7477
DOI: 10.1039/C8OB01733F

Social activity

Search articles by author

Spotlight

Advertisements