Electrochemical study of catechols in the presence of 4,6-dihydroxy-2-methylpyrimidine

Fakhari, Ali Reza; Nematollahi, Davood; Moghaddam, Abdolmajid Bayandori

doi:10.1016/j.jelechem.2004.11.032

Cited by 18 publications

(13 citation statements)

References 24 publications

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“…These results agreed with data obtained during the electrochemical oxidation of 3MC (Fakhari et al, 2005). Scheme 1 shows the reaction of 3MC with oxygen.…”

Section: Discussionsupporting

confidence: 90%

Investigation of toxic factors affecting cells of rat brains exposed to 3-methylcatechol

Barreto

Oliveira

Villar

et al. 2007

Braz. arch. biol. technol.

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“…These results agreed with data obtained during the electrochemical oxidation of 3MC (Fakhari et al, 2005). Scheme 1 shows the reaction of 3MC with oxygen.…”

Section: Discussionsupporting

confidence: 90%

Investigation of toxic factors affecting cells of rat brains exposed to 3-methylcatechol

Barreto

Oliveira

Villar

et al. 2007

Braz. arch. biol. technol.

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“…The electron-donating phenylethynyl groups decorating the central catechol unit in 1 most likely facilitate its oxidation. [69][70][71] Owing to the orthoformate-protecting group masking the catechol moiety, 17 shows no redox activity in the same potential range. In the case of rod 20 equipped with less labile tert-butylsulfanyl end groups, the behaviour of the catechol subunit is quite similar to that of 1, with an oxidation wave at +0.19 V and a reduction wave at +0.09 V (Figure 2, B).…”

Section: Electrochemistrymentioning

confidence: 99%

Redox‐Active Catechol‐Functionalized Molecular Rods: Suitable Protection Groups and Single‐Molecule Transport Investigations

Weibel

Błaszczyk²,

Hänisch³

et al. 2007

Eur J Org Chem

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The synthesis of molecular rod 1 comprising a central redox‐active unit and two terminal acetyl‐protected sulfur groups is reported. Various protecting groups for the catechol moiety were investigated and protected precursors 14–18 were synthesized. In particular, ethyl orthoformate 17 can be easily and selectively deprotected in mild acidic conditions ruling out the need for a strong Lewis acid like boron tribromide. The redox activity of 1 was confirmed by cyclic voltammetric investigations. Gold–molecule–gold junctions were formed with the dimethyl‐protected rod 18. Single‐molecule transport investigations using this molecular rod revealed a set of three single‐junction conductance values varying over two orders of magnitude.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

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“…Redox properties of some derivatives of these compounds in aqueous solutions is documented. [15][16][17][18][19][20][21][22] We thought that synthesis of a new 1,3-indandione derivatives with both structures of 1,3-indandione and hydroquinone would be useful from the point of view of pharmaceutical properties. This idea prompted us to development of a facile and environmentally friendly reagentless electrochemical method for the synthesis of some new 1,3-indandione derivatives in aqueous solutions with high atomic economy under ambient conditions and in an undivided cell using a graphite electrode and delineates the application of electrochemical studies in the design of an electrochemical method for the synthesis of new 1,3-indandione derivatives (5a-c).…”

Section: )mentioning

confidence: 99%

A Green Method for the Electroorganic Synthesis of New 1,3-Indandione Derivatives

Moghaddam

Norouzi

Latifi

2006

CHEMICAL & PHARMACEUTICAL BULLETIN

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On the other hand, it has been reported that ortho-and para-hydroquinones and their quinone derivatives are abundant in nature and play important roles in many biological systems. [7][8][9][10][11] In addition, many chemicals of this category demonstrate an antioxidant activity and are able to prevent auto-oxidation via the radical formation inhibition.12) These compounds exhibit a wide variety of physiological and pharmacological properties.13) They participate in normal cell functions such as neurotransmitters. Furthermore, natural pyrocatechols extracted from plants (catechins and other polyphenols from green tea) have been found to illustrate anticancer properties. 14)For these reasons, knowledge of the redox properties of these compounds is important for a better understanding of their behavior in biological environments. Redox properties of some derivatives of these compounds in aqueous solutions is documented. [15][16][17][18][19][20][21][22] We thought that synthesis of a new 1,3-indandione derivatives with both structures of 1,3-indandione and hydroquinone would be useful from the point of view of pharmaceutical properties. This idea prompted us to development of a facile and environmentally friendly reagentless electrochemical method for the synthesis of some new 1,3-indandione derivatives in aqueous solutions with high atomic economy under ambient conditions and in an undivided cell using a graphite electrode and delineates the application of electrochemical studies in the design of an electrochemical method for the synthesis of new 1,3-indandione derivatives (5a-c).Electroorganic Reactions of 4-tert-Butylcatechol (1a) and 4-Methylcatechol (1b) Figure 1, CV a displays the typical successive cyclic voltammogram (CV) of 0.25 mM 4-tert-butylcatechol (1a) in aqueous media (H 2 O : AN, 90 : 10), containing phosphate buffer (pHϭ7.0, cϭ0.15 M). This figure demonstrates one anodic peak (A 1 ) (at 0.291 V) and one corresponding cathodic peak (C 1 ) (at 0.105 V), which corresponds to the transformation of 4-tert-butylcatechol (1a) to o-quinone-4-tert-butyl (2a) and vice versa within a quasireversible two-electron and two-proton process (DEpϭ 0.186 V). 23,24) A peak current ratio (I P A1 /I P C1 ) of nearly unity, particularly during the repetitive potential recycle, can be considered as a criterion for the stability of o-quinone produced on the electrode surface under the experimental conditions. In other words, any hydroxylation 25,26) or dimerization 27,28) reactions are too slow to be observed on the time scale of the cyclic voltammetry.The oxidation of 4-tert-butylcatechol (1a) in the presence of 2-phenyl-1,3-indandione (3) (pK a ϭ4.1) 29) as a nucleophile was studied in detail. Figure 1, CV b presents the cyclic voltammogram obtained for a 0.25 mM solution of 1a in the presence of 0.25 mM 3. The corresponding voltammogram exhibits one anodic peak at 0.364 V (A 1 ) vs. the reference electrode, where the cathodic counterpart of the anodic peak A 1 decreases. In this condition, the positive shift of the A 1 p...

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Electrochemical study of catechols in the presence of 4,6-dihydroxy-2-methylpyrimidine

Cited by 18 publications

References 24 publications

Investigation of toxic factors affecting cells of rat brains exposed to 3-methylcatechol

Investigation of toxic factors affecting cells of rat brains exposed to 3-methylcatechol

Redox‐Active Catechol‐Functionalized Molecular Rods: Suitable Protection Groups and Single‐Molecule Transport Investigations

A Green Method for the Electroorganic Synthesis of New 1,3-Indandione Derivatives

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