Chemoselective synthesis of isolated and fused fluorenones and their photophysical and antiviral properties.
作者： Ismail Althagafi , Ranjay Shaw , Cheng-Run Tang , Rahul Panwar , Shally Shally
DOI: 10.1039/C8OB01733F
关键词: Solvent 、 Fluorescence 、 Amine gas treating 、 Yield (chemistry) 、 Ring (chemistry) 、 Reactivity (chemistry) 、 Lithium aluminium hydride 、 Chemistry 、 Terphenyl 、 Medicinal chemistry
摘要: Highly functionalized fluorenones were synthesized by an intramolecular cyclization of 2''-halo-[1,1':3',1''-terphenyl]-4'-carbonitriles in the presence n-butyllithium or lithium aluminium hydride. The precursor was ring transformation 2-oxo-6-aryl/heteroaryl-4-(sec.amino)-2H-pyran-3-carbonitriles 2-oxobenzo[h]chromenes with o-bromo/chloro/fluoro-acetophenone under basic conditions moderate yield. We performed control experiment to understand proposed mechanism and found that a secondary amine starting material directs reactivity. photophysical properties 3-methoxy-7-(piperidin-1-yl)-5H-indeno[2,1-b]phenanthren-8(6H)-one explored solvent dependent emission observed. These compounds also tested against HIV-1 low activity
rsc.org
sci-hub.se 参考文章(59)
Stephen R. D. George, Timothy E. Elton, Jason B. Harper, Electronic effects on the substitution reactions of benzhydrols and fluorenyl alcohols. Determination of mechanism and effects of antiaromaticity. Organic and Biomolecular Chemistry. ,vol. 13, pp. 10745- 10750 ,(2015) , 10.1039/C5OB01637A
Hashim F. Motiwala, Rakesh H. Vekariya, Jeffrey Aubé, Intramolecular Friedel–Crafts Acylation Reaction Promoted by 1,1,1,3,3,3-Hexafluoro-2-propanol Organic Letters. ,vol. 17, pp. 5484- 5487 ,(2015) , 10.1021/ACS.ORGLETT.5B02851
Kent A Nielsen, Ginka H Sarova, Luis Martín-Gomis, Fernando Fernández-Lázaro, Paul C Stein, Lionel Sanguinet, Eric Levillain, Jonathan L Sessler, Dirk M Guldi, Ángela Sastre-Santos, Jan O Jeppesen, Chloride anion controlled molecular "switching". Binding of 2,5,7-trinitro-9-dicyanomethylenefluorene-C60 by tetrathiafulvalene calix[4]pyrrole and photophysical generation of two different charge-separated states. Journal of the American Chemical Society. ,vol. 130, pp. 460- 462 ,(2008) , 10.1021/JA0772243
F. Uckert, Y.-H. Tak, K. Müllen, H. Bässler, 2,7‐Poly(9‐fluorenone): A Trap‐Free Electron‐Injection Material with a High Charge Carrier Mobility for Use in Light‐Emitting Diodes Advanced Materials. ,vol. 12, pp. 905- 908 ,(2000) , 10.1002/1521-4095(200006)12:12<905::AID-ADMA905>3.0.CO;2-W
Jochanan Blum, Zeev Lipshes, Catalytic conversion of benzoic anhydrides into fluorenones Journal of Organic Chemistry. ,vol. 34, pp. 3076- 3080 ,(1969) , 10.1021/JO01262A062
Jonathan R. Nitschke, Molecular networks come of age Nature. ,vol. 462, pp. 736- 738 ,(2009) , 10.1038/462736A
Sebastian Wertz, Dirk Leifert, Armido Studer, Cross Dehydrogenative Coupling via Base-Promoted Homolytic Aromatic Substitution (BHAS): Synthesis of Fluorenones and Xanthones Organic Letters. ,vol. 15, pp. 928- 931 ,(2013) , 10.1021/OL4000857
Xue Zhang, Jie-Kun Xu, Jue Wang, Nai-Li Wang, Hiroshi Kurihara, Sumumu Kitanaka, Xin-Sheng Yao, Bioactive bibenzyl derivatives and fluorenones from Dendrobium nobile. Journal of Natural Products. ,vol. 70, pp. 24- 28 ,(2007) , 10.1021/NP060449R
Yan-Fu Chen, Yi-Sheng Wu, Yu-Huei Jhan, Jen-Chieh Hsieh, An efficient synthesis of (NH)-phenanthridinones via ligand-free copper-catalyzed annulation Organic chemistry frontiers. ,vol. 1, pp. 253- 257 ,(2014) , 10.1039/C3QO00082F
Jonathan W. Lockner, Darryl D. Dixon, Rune Risgaard, Phil S. Baran, Practical radical cyclizations with arylboronic acids and trifluoroborates. Organic Letters. ,vol. 13, pp. 5628- 5631 ,(2011) , 10.1021/OL2023505