DNA-Binding Properties of Nonsymmetric Fluorenone Derivatives

Lyakhov, S. A.; Lyakhova, E. A.; Karpenko, Alexander S.; Maltsev, G. V.; Vel'cheva, I. V.; Litvinova, L. A.; Lebedyuk, M. N.; Хорохорина, Г. А.; Федчук, В. П.

doi:10.1023/b:phac.0000034300.89484.b1

Cited by 8 publications

(3 citation statements)

References 4 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Fluorene is a core structure of various useful and interesting compounds, such as MTP inhibitors,22 interferon inductors,23 and others 24. Fluorenes in polymer form have also attracted much attention as molecular devices for blue‐light‐emitting materials 25.…”

Section: Resultsmentioning

confidence: 99%

CC Coupling Reactions of Superstrong CF₃ Groups with C(sp²)–H Bonds: Reactivity and Synthetic Utility of Zero‐Valent Niobium Catalyst

Fuchibe

Mitomi

Suzuki

et al. 2008

Chemistry An Asian Journal

View full text Add to dashboard Cite

It was found that zero-valent niobium is an efficient catalyst for the intramolecular C-C coupling reactions of o-aryl and o-alkenyl alpha,alpha,alpha-trifluorotoluene derivatives. The superstrong C-F bonds of CF3 groups and neighboring C(sp2)-H bonds were doubly activated, and fluorenes and indenes were obtained in good yields. The niobium fluorocarbenoid species is proposed to be the key intermediate.

show abstract

Section: Resultsmentioning

confidence: 99%

CC Coupling Reactions of Superstrong CF₃ Groups with C(sp²)–H Bonds: Reactivity and Synthetic Utility of Zero‐Valent Niobium Catalyst

Fuchibe

Mitomi

Suzuki

et al. 2008

Chemistry An Asian Journal

View full text Add to dashboard Cite

show abstract

“…Fluorene is the core structure of potent molecules such as the blue-light emitting materials, 1 interferon inducers, 2 antitumor compounds, 3 and inhibitor of microsomal triglyceride-transfer protein. 4 9-Fluorenylidene structure has also been attracted and applied to a molecular motor for reorganization of cholesteric molecules, 5 organic field-effect transistor devices, 6 and pH sensors.…”

mentioning

confidence: 99%

Platinum- and Palladium-Catalyzed Sequential Reactions: Regioselective Synthesis of 9-Fluorenylidenes from 9-Ethynylfluoren-9-yl Carboxylates and Furans

Miki¹,

Senda²,

Kowada³

et al. 2009

Synlett

View full text Add to dashboard Cite

show abstract

“…Fluorene is the core structure of naturally occurring potent molecules such as the MTP inhibitor, 9 interferon inducers 10 and antitumor compounds. 11 Fluorenes in polymer structures have also attracted much attention as molecular devices for blue-light-emitting materials.…”

mentioning

confidence: 99%

Synthesis of 2-(9-Fluorenyl)acrylic Acid Derivatives via Intramolecular Friedel-Crafts Reaction of Morita-Baylis-Hillman Adducts of 2-Biphenylcarboxaldehydes

Lim¹,

Ji²,

Lee³

2007

Synthesis

View full text Add to dashboard Cite

Treatment of propiolic acid esters or N,N-dimethylpropynamide and various 2-biphenylcarboxaldehydes with tetrabutylammonium iodide/zirconium(IV) chloride, titanium(IV) chloride/ dimethyl sulfide, or titanium(IV) bromide/dimethyl sulfide or treatment of methyl acrylate and 2-biphenylcarboxaldehydes with 1,4-diazabicyclo[2.2.2]octane (DABCO) and triethanolamine induce an aldol-type reaction to furnish b-halo-a-(hydroxymethyl)acrylates or a-(hydroxymethyl)acrylates, respectively. These can be used for the preparation of 2-(9H-fluoren-9-yl)acrylic acid derivatives by intramolecular Friedel-Crafts reaction with sulfuric acid in tetrachloromethane.The Morita-Baylis-Hillman (MBH) chemistry has become one of the important and attractive sources for chemical transformations in synthetic organic chemistry and is of current interest. 1 The Friedel-Crafts reaction is one of the most fundamental carbon-carbon bond forming reaction in organic synthesis. 2 Recently, Basavaiah and Kim independently reported the syntheses of a variety of compounds from MBH adducts with the Friedel-Crafts reaction as the key step. These include syntheses of 2-benzylcinnamates, 3 indenes, 4 2-arylideneindan-1-ones, 5 indenoquinolines, 6 and 2-quinolones. 7 During continued efforts to develop MBH chemistry, 8 we envisioned that we could synthesize the fluorene derivatives 4 from MBH adducts of 2-biphenylcarboxaldehydes 2 by an intramolecular Friedel-Crafts reaction as shown in Scheme 1.Fluorene is the core structure of naturally occurring potent molecules such as the MTP inhibitor, 9 interferon inducers 10 and antitumor compounds. 11 Fluorenes in polymer structures have also attracted much attention as molecular devices for blue-light-emitting materials. 12 The 9-fluorenylmethoxycarbonyl (Fmoc) group has tremendous popularity as a protecting group for amines in the synthesis of peptides and related compounds. 13 Although there are numerous reports on the synthesis of fluorenes 14 including the Friedel-Crafts method, 15 there has not been a report on the Friedel-Crafts intramolecular cyclization of MBH adducts of 2-biphenylcarboxaldehydes to give fluorenes.The required b-iodo-MBH adducts 2a-e were prepared by the reaction of alkyl propiolates or N,N-dimethylpropynamide with tetrabutylammonium iodide, followed by an aldol process with aldehydes 1a-c in the presence of zirconium(IV) chloride in 55-81% yields, originally reported by Taniguchi 16 and Lu. 17,18 The b-chloro-MBH adduct 2f (52%) and b-bromo-MBH adduct 2g (22%) were obtained by the reaction of methyl propiolate with 2-biphenylcarboxaldehyde (1a) in the presence of titanium(IV) chloride/dimethyl sulfide or titanium(IV) bromide/dimethyl sulfide, respectively, according to the Kataoka procedure. 19 In the 1 H NMR spectra, the characteristic chemical shift of the alkenic protons of 2a-g were found at d = 6.43-7.18 as a doublet due to allylic coupling (J = 1.2-1.5 Hz). In all cases, the stereoselectivity was found to be 100% Z-selectivity, as determined by 1 H NMR analysis in comparison with li...

show abstract

DNA-Binding Properties of Nonsymmetric Fluorenone Derivatives

Cited by 8 publications

References 4 publications

CC Coupling Reactions of Superstrong CF₃ Groups with C(sp²)–H Bonds: Reactivity and Synthetic Utility of Zero‐Valent Niobium Catalyst

CC Coupling Reactions of Superstrong CF₃ Groups with C(sp²)–H Bonds: Reactivity and Synthetic Utility of Zero‐Valent Niobium Catalyst

Platinum- and Palladium-Catalyzed Sequential Reactions: Regioselective Synthesis of 9-Fluorenylidenes from 9-Ethynylfluoren-9-yl Carboxylates and Furans

Synthesis of 2-(9-Fluorenyl)acrylic Acid Derivatives via Intramolecular Friedel-Crafts Reaction of Morita-Baylis-Hillman Adducts of 2-Biphenylcarboxaldehydes

Contact Info

Product

Resources

About

DNA-Binding Properties of Nonsymmetric Fluorenone Derivatives

Cited by 8 publications

References 4 publications

CC Coupling Reactions of Superstrong CF3 Groups with C(sp2)–H Bonds: Reactivity and Synthetic Utility of Zero‐Valent Niobium Catalyst

CC Coupling Reactions of Superstrong CF3 Groups with C(sp2)–H Bonds: Reactivity and Synthetic Utility of Zero‐Valent Niobium Catalyst

Platinum- and Palladium-Catalyzed Sequential Reactions: Regioselective Synthesis of 9-Fluorenylidenes from 9-Ethynylfluoren-9-yl Carboxylates and Furans

Synthesis of 2-(9-Fluorenyl)acrylic Acid Derivatives via Intramolecular Friedel-Crafts Reaction of Morita-Baylis-Hillman Adducts of 2-Biphenyl­carboxaldehydes

Contact Info

Product

Resources

About

CC Coupling Reactions of Superstrong CF₃ Groups with C(sp²)–H Bonds: Reactivity and Synthetic Utility of Zero‐Valent Niobium Catalyst

CC Coupling Reactions of Superstrong CF₃ Groups with C(sp²)–H Bonds: Reactivity and Synthetic Utility of Zero‐Valent Niobium Catalyst

Synthesis of 2-(9-Fluorenyl)acrylic Acid Derivatives via Intramolecular Friedel-Crafts Reaction of Morita-Baylis-Hillman Adducts of 2-Biphenylcarboxaldehydes