Polyfunctional Tetrazolic Thioethers through Electrooxidative/Michael-Type Sequential Reactions of 1,2- and 1,4-Dihydroxybenzenes with 1-Phenyl-5-mercaptotetrazole

Khodaei, Mohammad Mehdi; Alizadeh, Abdolhamid; Pakravan, Narges

doi:10.1021/jo702327m

Cited by 46 publications

(24 citation statements)

References 28 publications

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“…The results revealed that the quinones derived from catechols participate in a Michael type addition reaction via an EC mechanism converted to the corresponding catechol derivatives. The electrochemical synthesis of various thiocatechol products (Table 2) has been successfully performed at a carbon rod electrode and in an undivided cell with good yields and high purity [18][19][20][21][22][23][24][25][26].…”

Section: C-s Bond Formationmentioning

confidence: 99%

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Mechanistic study of homogeneous reactions coupled with electrochemical oxidation of catechols

Nematollahi

Rafiee

Fotouhi

2009

JICS

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The electrochemical oxidation of catechols was described and has shown that these compounds can be oxidized to related obenzoquinones. The electrochemically generated o-benzoquinones are quite reactive and can be attacked by a variety of nucleophiles under various mechanistic disciplines such as CE, EC, EC ' , ECE, ECEC, ECEC 2 , ECECE, ECECEC, ECECECE and trimerization, in which E represents an electron transfer at the electrode surface, and C represents a homogeneous chemical reaction. The mechanistic pathways and final products are depending on some parameters such as electron withdrawing or donating properties of nucleophile, electrolysis medium (solvent, acidity or pH) and nature of catechol.

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Section: C-s Bond Formationmentioning

confidence: 99%

“…Some new C-phosphoniumquinol betaine compounds (23) were synthesized from a conjugated addition reaction of triphenylphosphine (22) to the electrochemically generated obenzoquinone via an EC mechanism (Scheme 6) [34].…”

Section: C-p Bond Formationmentioning

confidence: 99%

Mechanistic study of homogeneous reactions coupled with electrochemical oxidation of catechols

Nematollahi

Rafiee

Fotouhi

2009

JICS

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“…The precipitated solid was collected by filtration, washed copiously with distilled water and characterized by spectral data and were compared with those reported in the literature. 38,39) The final products (1A-5A, 1B-3B) were obtained purely and no extra purification was needed. 38,39) 4-tert-Butyl-5-(1-phenyl-1H-tetrazol-5-ylthio)benzene-1,2-diol (1A) 39) mp 181-183°C; yield 59%; IR (KBr) cm …”

Section: Methodsmentioning

confidence: 99%

“…1, the compound I derivatives has well-known antiviral and anti-inflammatory properties, 32,33) 1-aryl-thiotetrazolyl acetanilides (II, III) have demonstrated activities as human immunodeficiency virus-1 (HIV-1) non-nucleoside reverse transcriptase inhibitors, [34][35][36] and 1-phenyl-5-arylthiotetrazole (IV) is used as activating reagent in RNA synthesis. 37) Due to a broad spectrum of activities reported in the literature so far, we have prepared a number of catecholthioethers having benzoxazole 38) and tetrazole 39) moieties for evaluating their antimicrobial and antioxidant activities (Chart 1).…”

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confidence: 99%

Catecholthioether Derivatives: Preliminary Study of in-Vitro Antimicrobial and Antioxidant Activities

Adibi

Rashidi

Khodaei

et al. 2011

CHEMICAL & PHARMACEUTICAL BULLETIN

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In this research, synthesis, antimicrobial and antioxidant activities of a series of catecholthioethers having benzoxazole and tetrazole moieties are described. Antimicrobial activity was evaluated by minimum inhibitory concentration (MIC) assay. The synthesized compounds were tested in vitro against three Gram-positive bacteria including Staphylococcus aureus (clinical isolated), Staphylococcus aureus ATCC 25922, Enterococcus faecium (clinical isolated), and two Gram-negative bacteria including Klebsiella pneumoniae (clinical isolated) and Pseudomonas aeruginosa 27853 and the yeast Candida albicans in comparison with control drugs. Microbiological results indicated that the synthesized compounds possessed a broad spectrum of activity against the tested microorganisms at MIC values between 4-256 m mg/ml. This shows compounds having tetrazole moiety were the most active against Gram-negative strains, whereas compounds having benzoxazole moiety were more active against Gram-positive ones. Also both of them showed significant antifungal activity against Candida albicans and had lower activity than the compared control drugs (Sulfamethoxazole and Fluconazole). The antioxidant activity was assessed using two methods, including, 1,1-biphenyl-2-picrylhydrazyl (DPPH) radical scavenging, and reducing power assays. Some of the catecholthioether derivatives showed antioxidant activity more than Trolox and butylated hydroxyanisole (BHA) as reference antioxidants.

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“…In addition, they are major raw materials used in a wide range of applications including dyes, light stabilizers, electroplating materials, and antioxidants [1,2]. However, they are highly toxic compounds, with stimulatory effects on the central nervous and respiratory systems.…”

Section: Introductionmentioning

confidence: 99%

Preparation of flower-like Pd–graphene composites for simultaneous determination of catechol and hydroquinone

2015

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Substrate-selective flower-like Pd nanoparticles were prepared using a simple electrodeposition method. The flower-like Pd-graphene nanocomposites showed excellent electrochemical properties, as proven by electrochemical impedance and cyclic voltammetry. Developed to serve as a sensor for simultaneous determination of catechol (CT) and hydroquinone (HQ), the Pd-graphene nanocomposite-modified glassy carbon electrode (Pd-graphene/GCE) displayed good electrochemical catalytic activity toward CT and HQ, which was attributed to the flower-like composite structure, i.e. high electrical conductivity and larger surface area of Pd-graphene nanocomposites. Several kinetic parameters were calculated, including the electron transfer number (n), proton transfer number (m), charge transfer coefficient (c), and apparent heterogeneous electron transfer rate constant (ks). Under optimized conditions, the oxidation peak current was linear over a range from 0.075 to 5 mM. The detection limits were 1.25 9 10 -6 mol/L for HQ and 1.0 9 10 -6 mol/L for CT (S/N = 3). The proposed Pd-graphene/GCE was applied to the simultaneous determination of HQ and CT in Songshan Lake water samples.

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Polyfunctional Tetrazolic Thioethers through Electrooxidative/Michael-Type Sequential Reactions of 1,2- and 1,4-Dihydroxybenzenes with 1-Phenyl-5-mercaptotetrazole

Cited by 46 publications

References 28 publications

Mechanistic study of homogeneous reactions coupled with electrochemical oxidation of catechols

Mechanistic study of homogeneous reactions coupled with electrochemical oxidation of catechols

Catecholthioether Derivatives: Preliminary Study of in-Vitro Antimicrobial and Antioxidant Activities

Preparation of flower-like Pd–graphene composites for simultaneous determination of catechol and hydroquinone

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