Ferrocenyl pyrazolines: Preparation, structure, redox properties and DFT study on regioselective ring-closure

Zsoldos‐Mády, Virág; Ozohanics, Olivér; Csámpai, Antal; Kudar, Veronika; Frigyes, Dávid; Sohár, Pàl

doi:10.1016/j.jorganchem.2009.09.007

Cited by 21 publications

(7 citation statements)

References 36 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Pyrazoline 1 is a known compound and gave analytical data in agreement with published results . Pyrazolines 2 and 3 are novel compounds prepared using analogous procedures.…”

Section: Figuresupporting

confidence: 81%

See 1 more Smart Citation

Redox‐Enabled, pH‐Disabled Pyrazoline–Ferrocene INHIBIT Logic Gates

et al. 2017

View full text Add to dashboard Cite

Pyrazoline-ferrocene conjugatesw ith an "electron-donorspacer-fluorophore-receptor" format are demonstrated as redox-fluorescent two-input INHIBIT logic gates.Molecular logic-basedc omputation is now firmly established as am aturing research discipline with researchers contemplating pragmatic uses for this curiosity-based science. [1][2][3][4][5] Medicalrelated innovations such as photodynamic photosensitizers, [6] drug delivery systems [7] and multi-analyte diagnostics [8] are but af ew envisioned applications. One of our visions is the realization of logic gates responsive to the physiochemical parameters of pH and potential( pE), which are fundamental to understanding metal ion solubility in geology and metallurgy as well as in medicine. [9] The development of reliable fluorescentc hemosensors and logic gates for open-shell d-metal ions, particularly Fe 3 + ,r equires overcoming several challenges including issues of solubility.[10] The vast majority of studies in this field continuet ob e reported in organic solvents, where Fe 3 + can form aqua-coordinated speciest hat act as unsuspecting weak acids.[11] Consequently,c omplexation or redox chemistry is often inferred, when matter-of-fact the fluorescent response is due to acidbase chemistry.[12] Furthermore, it is commonly taken for granted that in water Fe 3 + hydrolyses to insoluble Fe(OH) 3 above pH 4. [13] With an understanding of these issues, [10] the applicability of pE-pH logic gates in an applied setting is ar eal possibility.F or example, the detection of Fe 3 + under acidic conditions by fluorescencec ould become ar outine method for the early detection of corrosion of ferrous alloys such as steel. [14] Wu and colleagues have demonstrated an oteworthy logic gate responsive to pH andr edox chemistry.[15] The prototype consisted of ad imethylaniline moiety (protonr eceptor) attached to aP t II complexedt erpyridyl (by av irtual spacer) linked to af errocenyl acetylide (electron donor). From ad esign point of view,t his molecule exemplifies am olecular device with an "electron-donor-fluorophore-spacer-receptor" format. The logic gate exhibited an INHIBIT function with H + and Fe 3 + as the inputs and absorbance at 405 nm as the output. The mechanism of operation involved photoinduced electron transfer (PET) from the dimethylaniline unit and am etal-toligand charget ransfer from the ferrocenyl acetylide. Understandably,b eing ap roof-of-concept, the study wasp erformed in acetonitrile.Herein we now presente xamples of pyrazoline-ferrocene conjugates 1-3 with an ovel "electron-donor-spacer-fluorophore-receptor" format for the first time (Figure 1). In contrast to the example by Wu, we illustrate pE-pH INHIBIT logic gates with an ew structuralc onfiguration (the spaceri sl ocated between the electron donor and fluorophore rather than between the fluorophore and receptor) with fluorescencer ather than absorbance as the output and in 1:1( v/v)m ethanol/water rather than in acetonitrile.At the 5-position of the pyrazoline ring, 1-3 have aferrocene (electro...

show abstract

“…Pyrazoline 1 is a known compound and gave analytical data in agreement with published results . Pyrazolines 2 and 3 are novel compounds prepared using analogous procedures.…”

Section: Figuresupporting

confidence: 81%

“…Pyrazoline 1 is ak nown compound and gave analytical data in agreement with published results. [38,39] Pyrazolines 2 and 3 are novel compounds prepared using analogous procedures. Characterisation data for 1-3 are provided in the Supporting Information.…”

Section: Methodsmentioning

confidence: 99%

Redox‐Enabled, pH‐Disabled Pyrazoline–Ferrocene INHIBIT Logic Gates

et al. 2017

View full text Add to dashboard Cite

show abstract

“…Considerable interest has been focused in their broad range of biological activities such as antibacterial [20], antitumour [21], antioxidant [22], antihyperglycemic [23] and anti-HIV [24]. Very recently, ferrocenyl chalcones have also been studied with regard to their nematocidal activities [25], fluorescent and electrochemical properties [26] as well as radicalscavenging capacities [27], molecular chemosensor activities [28] and as precursors for the syntheses of ferrocenyl pyrazolines [29,30]. Ferrocenyl chalcones have been conveniently prepared by a base-catalysed ClaiseneSchmidt condensation between acetylferrocene and an appropriately substituted aromatic aldehyde or ferrocene aldehyde and an appropriately substituted aromatic ketone.…”

Section: Introductionmentioning

confidence: 99%

Cyrhetrenyl chalcones: Synthesis, characterization and antimalarial evaluation

Arancibia

Biot

Delaney

et al. 2013

Journal of Organometallic Chemistry

View full text Add to dashboard Cite

“…For example, when G = aroyl group, cyclization occurs in the presence of acetic anhydride to give 1,3,4-oxadiazoles [1,23,24,25,26]. On the other hand, when G = carboxamide or aryl group, cyclization with acetic anhydride gave exclusive formation of pyrazole derivatives [2,27,28]. Finally, treatment of chalcones 1a-f with semicarbazide hydrochloride in dioxane containing few drops of acetic acid gave pyrazolines 5a-f in good yields.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and in Vitro Antimicrobial Activity of Some Pyrazolyl-1-carboxamide Derivatives

Sharshira

Hamada

2011

Molecules

View full text Add to dashboard Cite

A series of 3,5-disubstituted pyrazole-1-carboxamides were obtained by treatment of chalcones with semicarbazide hydrochloride in dioxane containing sodium acetate/acetic acid as a buffer solution. N-acetyl derivatives of pyrazole-1-carboxamides were isolated in good yields either by treatment of the carboxamide derivatives with acetic anhydride or refluxing chalcones with semicarbazide in ethanol containing few drops of acetic acid to give the corresponding hydrazones. Subsequent treatment of hydrazones with acetic anhydride gave the desired N-acetyl pyrazole-1-carboxamides derivatives. When chalcones were refluxed with dioxane containing few drops of acetic acid, 4,5-dihydropyrazole-1-carboxamides were isolated, which were subsequently oxidized using 5% sodium hypochlorite in dioxane to afford pyrazole-1-carboxamides. The structures of isolated compounds were confirmed by elemental analyses and spectral methods. The isolated compounds were tested for their antimicrobial activities.

show abstract

Ferrocenyl pyrazolines: Preparation, structure, redox properties and DFT study on regioselective ring-closure

Cited by 21 publications

References 36 publications

Redox‐Enabled, pH‐Disabled Pyrazoline–Ferrocene INHIBIT Logic Gates

Redox‐Enabled, pH‐Disabled Pyrazoline–Ferrocene INHIBIT Logic Gates

Cyrhetrenyl chalcones: Synthesis, characterization and antimalarial evaluation

Synthesis and in Vitro Antimicrobial Activity of Some Pyrazolyl-1-carboxamide Derivatives

Contact Info

Product

Resources

About