4.4 Article

Electrochemical study of catechols in the presence of 2-thiazoline-2-thiol: application to electrochemical synthesis of new 4,5-dihydro-1,3-thiazol-2-ylsulfanyl-1,2-benzenediol derivatives

Journal

JOURNAL OF APPLIED ELECTROCHEMISTRY
Volume 38, Issue 12, Pages 1743-1747

Publisher

SPRINGER
DOI: 10.1007/s10800-008-9625-0

Keywords

Electrochemical synthesis; EC mechanism; Catechol; 2-Thiazoline-2-thiol

Funding

  1. Shahid Beheshti University

Ask authors/readers for more resources

Electrochemical oxidation of catechols (1a-d) has been studied in the presence of 2-thiazoline-2-thiol (3) as a nucleophile in aqueous solution, using cyclic voltammetry and controlled potential coulometry. The results indicate that the quinones derived from catechols (1a-d), participate in Michael addition reactions with 2-thiazoline-2-thiol and via an EC mechanism pathway, convert to the corresponding catechols derivatives (4a-d and 4'd). The electrochemical synthesis of compounds (4a-d and 4'd) has been successfully performed at a carbon rod electrode and in an undivided cell with good yield and high purity. The products have been characterized by IR, 1H NMR, 13C NMR and MS.

Authors

I am an author on this paper
Click your name to claim this paper and add it to your profile.

Reviews

Primary Rating

4.4
Not enough ratings

Secondary Ratings

Novelty
-
Significance
-
Scientific rigor
-
Rate this paper

Recommended

Article Biochemistry & Molecular Biology

Green pseudo-multicomponent synthesis of some new spirocyclopropane derivatives via electro-catalyzed reaction

Ali Asghar Mohammadi, Somayeh Makarem, Reza Ahdenov, Nazila Amiri Notash

MOLECULAR DIVERSITY (2020)

Article Chemistry, Organic

Three-component electrosynthesis of spirooxindole-pyran derivatives through a simple and efficient method

Somayeh Makarem

JOURNAL OF HETEROCYCLIC CHEMISTRY (2020)

Article Biochemistry & Molecular Biology

Electro-organic synthesis of tetrahydroimidazo[1,2-a]pyridin-5(1H)-one via a multicomponent reaction

Mohammad Reza Asghariganjeh, Ali Asghar Mohammadi, Elham Tahanpesar, Ayeh Rayatzadeh, Somayeh Makarem

Summary: A series of novel tetrahydroimidazo[1,2-a]pyridine-5(1H)-one derivatives containing an electronegative pharmacophore (=CNO2) were successfully synthesized through a one-pot three-component condensation. The green protocol, carried out in a propanol medium with sodium bromide as electrolyte, showed great potential for the synthesis of fused polycyclic structures related to bioactive heterocycles.

MOLECULAR DIVERSITY (2021)

Article Chemistry, Multidisciplinary

Simultaneous separation and quantification of acidic and basic dye specimens via a dual gel electro-membrane extraction from real environmental samples

Samira Mohammad Rezaei, Somayeh Makarem, Michal Alexovic, Hadi Tabani

Summary: An environmentally friendly and easy-to-use dual gel electro-membrane extraction method was developed for parallel determination of basic and acidic dyes, showing high selectivity and no need for hazardous organic solvents. The method demonstrated high extraction efficiencies, low detection limits, and successful application in complex environmental samples.

JOURNAL OF THE IRANIAN CHEMICAL SOCIETY (2021)

Article Chemistry, Analytical

Gelatin microsphere coated Fe3O4@graphene quantum dots nanoparticles as a novel magnetic sorbent for ultrasound-assisted dispersive magnetic solid-phase extraction of tricyclic antidepressants in biological samples

Zolfaghar Aladaghlo, Siamak Javanbakht, Ali Reza Fakhari, Ahmad Shaabani

Summary: A novel sorbent, Fe3O4@GQD@GM, was designed and synthesized for trace determination of three tricyclic antidepressants. The proposed method showed excellent linearity, sensitivity, and repeatability under optimized conditions. This method was successfully applied for determination of the antidepressants in various biological samples.

MICROCHIMICA ACTA (2021)

Article Chemistry, Multidisciplinary

Organobase-catalyzed one-pot three-component synthesis of novel pyrano[2,3-d][1,3]thiazolo[3,2-a]pyrimidine derivatives

Abbas Ali Esmaeili, Fariba Mesbah, Mandieh Zangouei, Saeid Amini-Ghalandarabad, Masoud Tasmimi, Azizollah Habibi, Ali Reza Fakhari, Amir Khojastehnezhad

Summary: An efficient and rapid method has been developed for the synthesis of a novel type of pyrano[2,3-d][1,3]thiazolo[3,2-a]pyrimidine derivatives through a three-component condensation reaction, with isolated yields of 90-94% achieved in short reaction times (5-10 min).

RESEARCH ON CHEMICAL INTERMEDIATES (2021)

Article Chemistry, Multidisciplinary

Magnetic MWCNT@guanidine acetic acid@Cu as a nanosorbent for ultrasonic assisted dispersive magnetic solid phase extraction of heterocyclic pesticides in citrus samples

Zolfaghar Aladaghlo, Ali Reza Fakhari, Ahmad Shaabani

Summary: In this study, a novel nanosorbent was designed and synthesized for trace detection of heterocyclic pesticides in citrus fruit samples using corona discharge ion mobility spectrometry. The method showed good extraction efficiency, linearity, repeatability, and sensitivity. It provides a reliable approach for pesticide analysis in citrus fruits.

JOURNAL OF THE IRANIAN CHEMICAL SOCIETY (2022)

Article Chemistry, Multidisciplinary

The comparison of some chiral selectors for enantioselective separation of naproxen as a model drug in capillary electrophoresis: Thermodynamic analysis of the separation mechanism

Elahe Naghdi, Ali Reza Fakhari

Summary: The experiments demonstrated that vancomycin is the most effective chiral selector for enantiomeric separation, with different thermodynamic mechanisms compared to Hp-β-CD. The chiral discrimination behavior of naproxen in vancomycin-mediated CE is mainly influenced by electrostatic interactions, while inclusion complexation with Hp-β-CD plays a crucial role in enantioseparation.

JOURNAL OF THE IRANIAN CHEMICAL SOCIETY (2022)

Article Chemistry, Multidisciplinary

Application of amine-functionalized mesostructured cellular foam assisted electromembrane extraction for the determination of tramadol and methadone from urine samples

Ali Reza Fakhari, Seyedeh Mahsa Safavi, Ardeshir D. Yeganeh, Mostafa M. Amini, Ali Sahragard

Summary: The study utilized amine functionalized mesostructured cellular foam as a new support for electromembrane extraction, combined with corona discharge ion mobility spectrometer analysis, to simultaneously extract and quantify tramadol and methadone from human urine samples. The method had high recoveries, sensitivity, and proved to be applicable for determining model drugs in urine samples.

JOURNAL OF THE IRANIAN CHEMICAL SOCIETY (2022)

Article Chemistry, Multidisciplinary

Application of carbon nanotubes assisted electromembrane extraction technique followed with capillary electrophoresis for sensitive determination of cocaine in wastewater and biological samples

Ali Sahragard, Ali Reza Fakhari, Kobra Sadat Hasheminasab, Zolfaghar Aladaghlo

Summary: In this study, a carbon nanotubes assisted electromembrane extraction method (CNTs/EME) coupled with capillary electrophoresis (CE) was developed for the preconcentration and determination of cocaine in various real samples. The CNTs/EME method provided higher extraction efficiencies at a lower extraction voltage compared to the EME method. The optimized conditions achieved a wide linear range of 7-3000 ng mL(-1), a low detection limit of 2.12 ng mL(-1), and high preconcentration factor, extraction recovery, and repeatability. The method was successfully applied to determine cocaine in wastewater and biological samples.

JOURNAL OF THE IRANIAN CHEMICAL SOCIETY (2023)

Article Chemistry, Applied

Cellulose-based nanocomposite for ultrasonic assisted dispersive solid phase microextraction of triazole fungicides from water, fruits, and vegetables samples

Zolfaghar Aladaghlo, Siamak Javanbakht, Ali Sahragard, Ali Reza Fakhari, Ahmad Shaabani

Summary: An ultrasound-assisted dispersive solid phase microextraction (UA-DSPME) approach was developed for trace level analysis of triazole fungicides in real samples. By using a newly prepared nanosorbent and optimizing extraction parameters, this method achieved good analysis performance.

FOOD CHEMISTRY (2023)

Article Biochemical Research Methods

Carboxymethylated maltodextrin as a chiral selector for the separation of some basic drug enantiomers using capillary electrophoresis

Mustafa Alawadi, Ali Reza Fakhari, Mohammad Reza Bayatloo, Saeed Nojavan

Summary: In this study, carboxymethylated maltodextrin (Cm-MD) was synthesized as an efficient anionic chiral selector and used for enantiomer separation of basic drugs by capillary electrophoresis. Cm-MD modified CE method achieved successful enantiomer separation with higher resolution compared to MD modified CE.

JOURNAL OF CHROMATOGRAPHY A (2023)

Article Chemistry, Analytical

Fabrication of Co3O4 quantum dot incorporated polyacrylamide ethylene glycol dimethacrylate as a new fiber for solid phase microextraction and trace determination of organophosphorus pesticides in environmental water samples

Zolfaghar Aladaghlo, Bozorgmehr Maddah, Ali Reza Fakhari

Summary: This paper presents a novel solid phase microextraction fiber based on Co3O4 quantum dot incorporated polyacrylamide-co-ethylene glycol dimethacrylate followed by corona discharge ion mobility spectrometry for the trace determination of organophosphorus pesticides in environmental water samples. The method offers low limits of detection, excellent enrichment factors, good linearity, and repeatability.

ANALYTICAL METHODS (2021)

No Data Available