Syntheses Related to Etiojervane. II. Synthesis of Some Substituted Fluorenes

Barnes, Roderick A.; Faessinger, Robert W.

doi:10.1021/jo01069a083

Cited by 14 publications

(6 citation statements)

References 2 publications

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“… Fluorene was converted in 61% yield into 2,7-diacetylfluorene ( 13 ), which was then subjected to Baeyer–Villiger oxidation to give diacetate 14 in 60% yield. Subsequent hydrolysis provided 2,7-dihydroxyfluorene ( 15 ) in 98% yield, ,− and oxidation with PIDA in MeOH produced fluorenequinone 9 as a reactive red solid in 85% yield.…”

Section: Resultsmentioning

confidence: 99%

Diphenoquinones Redux

et al. 2022

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Benzoquinones can undergo reversible reductions and are attractive candidates for use as active materials in green carbon-based batteries. Related compounds of potential utility include 4,4′-diphenoquinones, which have extended quinonoid structures with two carbonyl groups in different rings. Diphenoquinones are a poorly explored class of compounds, but a wide variety can be synthesized, isolated, crystallized, and fully characterized. Experimental and computational approaches have established that typical 4,4′-diphenoquinones have nearly planar cores in which two cyclohexadienone rings are joined by an unusually long interannular CC bond. Derivatives unsubstituted at the 3,3′,5,5′-positions react readily by hydration, dimerization, and other processes. Association of diphenoquinones in the solid state normally produces chains or sheets held together by multiple C–H···O interactions, giving structures that differ markedly from those of the corresponding 4,4′-dihydroxybiphenyls. Electrochemical studies in solution and in the solid state show that diphenoquinones are reduced rapidly and reversibly at potentials higher than those of analogous benzoquinones. Together, these results help bring diphenoquinones into the mainstream of modern chemistry and provide a foundation for developing redox-active derivatives for use in carbon-based electrochemical devices.

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Section: Resultsmentioning

confidence: 99%

Diphenoquinones Redux

et al. 2022

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“…General : Chlorohydrins ( 2 ) and ( 3 ), and triethylene glycol bistosylate are commercially available and were used as received. 2,7‐Dioxy‐9 H ‐fluoren‐9‐one ( 1 ),8 chlorohydrin ( 4 ),25 2,7‐dimethoxy‐9 H ‐fluoren‐9‐one ( 17 )26 and 2‐hydroxy‐7‐methoxy‐9 H ‐fluoren‐9‐one27 were prepared as described. Thin‐layer chromatography (TLC) was carried out on aluminum sheets coated with silica gel 60F (Merck 5554).…”

Section: Methodsmentioning

confidence: 99%

Bis(oxofluorenediyl)oxacyclophanes: Synthesis, Crystal Structure and Complexation with Paraquat in the Gas Phase

Luk’yanenko

Kirichenko

Lyapunov

et al. 2004

Chemistry A European J

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The first three representatives of the new family of oxacyclophanes incorporating two 2,7-dioxyfluorenone fragments, connected by [-CH(2)CH(2)O-](m) spacers (m=2-4), have been synthesized. The yield of the smallest oxacyclophane (m=2) is considerably higher with respect to the larger ones (m=3 and m=4), which are formed in comparable yields. Molecular modeling and NMR spectra analysis of the model compounds suggest that an essential difference in oxacyclophanes yields is caused by formation of quasi-cyclic intermediates, which are preorganized for macrocyclization owing to intramolecular pi-pi stacking interactions between the fluorenone units. The solid-state structures of these oxacyclophanes exhibit intra- and intermolecular pi-pi stacking interactions that dictate their rectangular shape in the fluorenone backbone and crystal packing of the molecules with the parallel or T-shape arrangement. The crystal packing in all cases is also sustained by weak C--HO hydrogen bonds. FAB mass spectral analysis of mixtures of the larger oxacyclophanes (m=3 and m=4) and a paraquat moiety revealed peaks corresponding to the loss of one and two PF(6) (-) counterions from the 1:1 complexes formed. However, no signals were observed for complexes of the paraquat moiety with the smaller oxacyclophane (m=2). Computer molecular modeling of complexes revealed a pseudorotaxane-like incorporation of the paraquat unit, sandwiched within a macrocyclic cavity between the almost parallel-aligned fluorenone rings of the larger oxacyclophanes (m=3 and m=4). In contrast to this, only external complexes of the smallest oxacyclophane (m=2) with a paraquat unit have been found in the energy window of 10 kcal mol(-1).

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“…[12] Etiojervane is a testosterone analog and etiojervane related compound 11 ( Figure 1) has been synthesized from substituted fluorenone intermediates. [13]…”

Section: Fluorenone Derivatives As Antiviral Agentsmentioning

confidence: 99%

“…Selaginpulvilin C and D were synthesized from substituted fluorenone intermediates. The ethanolic extract contains Selaginpulvilin A, B, C, D (12)(13)(14)(15), and other constituents that showed phosphodiesterase-4 (PDE4) inhibitory activities ranging from 0.11 μM to 5.13 μM ( Figure 1). [14]…”

Section: Fluorenones Derivatives As Phosphodiesterase Inhibitorsmentioning

confidence: 99%

A Perspective on Synthesis and Applications of Fluorenones

et al. 2020

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Fluorenones are important constituents in material, medical and chemical sciences with potential applications in various domains. The key factors responsible for the diverse usage of fluorenones in material sciences are their intriguing and tunable photo, as well as physico‐chemical properties. Besides this, the presence of conjugated poly‐(en)ynes in the fluorenones makes them molecules of interest in material sciences. Fluorenones show various biological activities like antibiotics, anticancer, antiviral, and neuromodulatory, etc. Organic chemists are developing various protocols for the synthesis of fluorenones. Despite several protocols developed for their synthesis since 1931, there is no review covering their entire synthetic protocols. This review includes several classical and novel synthetic approaches for the synthesis of fluorenones. Furthermore, we delineated the mechanism by which they have been synthesized.

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Syntheses Related to Etiojervane. II. Synthesis of Some Substituted Fluorenes

Cited by 14 publications

References 2 publications

Diphenoquinones Redux

Diphenoquinones Redux

Bis(oxofluorenediyl)oxacyclophanes: Synthesis, Crystal Structure and Complexation with Paraquat in the Gas Phase

A Perspective on Synthesis and Applications of Fluorenones

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