Article
Chemistry, Organic
Michal Kopyt, Michal Tryniszewski, Michal Barbasiewicz, Piotr Kwiatkowski
Summary: Enantioselective Michael addition under high-pressure conditions is an efficient method to synthesize chiral cyclohexanes.
Article
Chemistry, Multidisciplinary
Xue Sun, Jianjing Yang, Kelu Yan, Xinyu Zhuang, Jie Yu, Xiaodan Song, Fanjun Zhang, Bingwen Li, Jiangwei Wen
Summary: This study presents a straightforward and practical strategy for hydrophosphorylation of electron-deficient alkenes and alkynes to access gamma-ketophosphine oxides. The strategy involves a convergent paired electrolysis (CPE) in the absence of a metal, base, and redox reagent. Mechanistic studies have revealed the dual role of diarylphosphane oxides as phosphorus radical precursors and hydrogen donors in this transformation.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Multidisciplinary
Jiahua Chen, Jun Wei Lim, Derek Yiren Ong, Shunsuke Chiba
Summary: The synthesis of alpha-tertiary amines was achieved by iteratively adding carbon nucleophiles to N,N-dialkyl carboxamides, forming anionic tetrahedral carbinolamine intermediates. These intermediates were then treated with bromotrimethylsilane followed by organomagnesium or organolithium reagents to produce alpha-tertiary amines. The use of (trimethylsilyl)methylmagnesium bromide as the second nucleophile allowed for aza-Peterson olefination, resulting in the formation of 1,1-diarylethylenes after acidic work-up.
Article
Polymer Science
Xiaoxia Yang, Hongyan Xie, Zhiguang Xu, Jiabing Feng, Qiwei Fu, Haidong Li, Yongtang Jia
Summary: An efficient method for synthesizing cyano-rich polyesters has been established by studying the catalytic performance of organic bases in Michael addition polymerization. The high-molecular-weight polyesters obtained display programmable thermal and mechanical properties.
JOURNAL OF POLYMER SCIENCE
(2021)
Article
Chemistry, Analytical
Mahmood Masoudi Khoram, Niloofar Mohamadighader, Davood Nematollahi, Sadegh Khazalpour, Hossein Masoumi, Hojjat Alizadeh
Summary: A green electrochemical method was developed for the synthesis of new spiro and dispiro pyrimidine derivatives. The reactivity of the nucleophile (barbituric acids) was found to be crucial in determining the type of product. The synthesized compounds showed good antibacterial performance against gram-positive bacteria.
JOURNAL OF ELECTROANALYTICAL CHEMISTRY
(2022)
Article
Chemistry, Applied
Kenya Tamaribuchi, Jiaqi Tian, Kengo Akagawa, Kazuaki Kudo
Summary: Enantioselective Michael addition of beta-dicarbonyl compounds towards nitroalkenes was achieved using an immobilized, N-terminal-guanidinylated peptide catalyst. Various nucleophiles and electrophiles were employed, with the resin-supported catalyst being recyclable for five cycles. This method shows promise for industrial applications.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Analytical
Yanhong Niu, Yangguang Li, Fanpeng Ma, Manman Zhang, Xuan Chen, Bang-Ce Ye
Summary: A stable ratiometric electrochemical sensing platform using nitrogen-doped MOF pyrolysis-derived CoNi/C (N-CoNi/C) and methylene blue (MB) was developed for the determination of p-phenylenediamine (PPD). The platform demonstrated good sensing performance with a linear relationship between electrical signal and PPD concentration in the range of 0.3-100 mu M, a correlation coefficient of 0.9987, and a detection limit of 0.091 mu M (S/N = 3). The sensor also showed successful application in the determination of PPD in commercial hair dyes with a recovery rate of over 95%.
Article
Chemistry, Applied
Jyoti M. Honnanayakanavar, Purna Chandra Behera, Surisetti Suresh
Summary: This study discloses a copper-catalyzed tandem process that integrates N-arylation and 1,4-conjugate addition using cyclic enaminones and ortho-halochalcones as substrates, resulting in the formation of diverse tricyclic tetrahydroacridinone derivatives in moderate to excellent yields.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Electrochemistry
Mahmood Masoudi-Khoram, Mitra Zargarian, Davood Nematollahi, Mohammad Ali Zolfigol, Hassan Sepehrmansourie, Sadegh Khazalpour
Summary: A green convergent paired electrochemical method was developed for the synthesis of bis-beta-diketones via Knoevenagel condensation reaction. Primary alcohols were electrochemically oxidized to aldehydes at the anode, and beta-diketones were reduced to active methylene compounds at the cathode. The cathodically activated methylene then reacted with the anodically generated aldehyde. Different types of bis-beta-diketones were synthesized using various primary alcohols and beta-diketones. This method provides a new strategy for mild and catalyst-free synthesis of a wide range of products in an undivided cell.
ELECTROCHIMICA ACTA
(2023)
Article
Chemistry, Physical
Fangfang Guo, Jiean Chen, Yong Huang
Summary: Recently, chiral N-heterocyclic carbenes (NHCs) have been established as powerful catalysts for enantioselective bond-forming processes via noncovalent interactions. A bifunctional NHC with an embedded hydrogen-bonding motif has been reported in this study, showing remarkable tolerance of various Michael acceptors in an asymmetric aza-conjugate addition reaction, with catalytic efficiency far exceeding that of the benchmark tertiary amine-thiourea scaffold.
Article
Chemistry, Organic
Shuting Tan, Jian-Guo Liu, Ming-Hua Xu
Summary: A rhodium-catalyzed asymmetric 1,4-addition reaction provides a practical approach for synthesizing highly enantioenriched chiral N-alkylindoles.
Article
Chemistry, Multidisciplinary
En Li, Jiean Chen, Yong Huang
Summary: The Michael reaction is an important method for preparing functional molecules with a β-stereogenic center. However, the enantioselective seleno-Michael addition is still poorly explored. In this study, a highly enantioselective Michael addition reaction of alkyl selenols to enones was reported, introducing a Se atom asymmetrically to an electron-deficient double bond. A chiral bifunctional N-heterocyclic carbene (NHC)/thiourea catalyst was developed and showed remarkable selectivity in delivering chiral β-seleno ketones.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Physical
Zhi-Ying Gong, Cheng-Li Yang, Dan Wang, Lang Huang, Zhi-Bing Dong
Summary: An efficient and convenient one-pot synthesis of benzoxazole/benzothiazole-substituted esters is achieved through a selective Michael addition reaction. This protocol offers high selectivity, good functional tolerance, mild conditions, and excellent yields, demonstrating its potential for the preparation of biologically and pharmaceutically active compounds.
Article
Chemistry, Physical
Viktoria Kozma, Zsolt Szakonyi, Gyorgy Szollosi
Summary: This study reveals the structural effects of beta-amino acids on the asymmetric Michael additions, including the impact of substituent bulkiness on selectivity, the beneficial arrangement of functional groups in cis isomers, and the influence of nitrogen substituents on reaction rate and enantioselectivity.
Article
Biochemistry & Molecular Biology
Jianqi Geng, Xingfu Wei, Biru He, Yuting Hao, Jingping Qu, Baomin Wang
Summary: The desymmetrization of N-pyrazolyl maleimides was successfully achieved through an asymmetric Michael addition using pyrazolones. It resulted in a high-yielding (up to 99% yield) formation of a tri-N-heterocyclic pyrazole-succinimide-pyrazolone assembly with excellent enantioselectivities (up to 99% ee). The use of a quinine-derived thiourea catalyst was crucial for stereocontrol of the vicinal quaternary-tertiary stereocenters and the C-N chiral axis.
Article
Chemistry, Analytical
Razzagh Rahimpoor, Abdulrahman Bahrami, Davood Nematollahi, Farshid Ghorbani Shahna, Maryam Farhadian
Summary: In this study, a magnetic-dispersive solid-phase extraction (DSPE) method was developed for the extraction and desorption of muconic acid from real urine samples. Fe3O4-SiO2-NH2@ UiO-66 was used as a Metal-Organic Framework (MOF) in the DSPE for extraction followed by HPLC analysis. The method showed good detection limit, wide linear dynamic range, and high correlation coefficient, indicating its efficiency for the extraction and analysis of muconic acid from urine samples.
INTERNATIONAL JOURNAL OF ENVIRONMENTAL ANALYTICAL CHEMISTRY
(2022)
Article
Electrochemistry
Niloofar Mohamadighader, Davood Nematollahi, Mahnaz Saraei
Summary: The electrochemical oxidation of propofol in a water/acetonitrile mixture was studied, revealing a chemically irreversible oxidation process to form propofol dimer. The electrochemical synthesis of PDQ was successfully achieved with the catalytic effect of sulfite ions. This method provides a greener alternative for dimerization of propofol under mild conditions.
JOURNAL OF THE ELECTROCHEMICAL SOCIETY
(2021)
Article
Chemistry, Analytical
Mahmood Masoudi Khoram, Niloofar Mohamadighader, Davood Nematollahi, Sadegh Khazalpour, Hossein Masoumi, Hojjat Alizadeh
Summary: A green electrochemical method was developed for the synthesis of new spiro and dispiro pyrimidine derivatives. The reactivity of the nucleophile (barbituric acids) was found to be crucial in determining the type of product. The synthesized compounds showed good antibacterial performance against gram-positive bacteria.
JOURNAL OF ELECTROANALYTICAL CHEMISTRY
(2022)
Article
Multidisciplinary Sciences
Zahra Souri, Mahmood Masoudi Khoram, Davood Nematollahi, Mohammad Mazloum-Ardakani, Hojjat Alizadeh
Summary: Electrochemical oxidation of imipramine in aqueous solutions was studied, showing a complex behavior at different pH values. The oxidation of imipramine at a pH of about 5 led to the formation of a unique dimer, which was fully characterized. A possible reaction mechanism for the oxidation process was proposed. The synthesized dimer exhibited fluorescence activity and good antibacterial performance.
SCIENTIFIC REPORTS
(2022)
Article
Electrochemistry
Faezeh Zivari-Moshfegh, Davood Nematollahi
Summary: A new derivative of desloratadine (DQ-TBC complex) was synthesized for the first time using a green electrochemical method. The electrooxidation of 4-tert-butylcatechol (TBC) in the presence of desloratadine (DES) was investigated to optimize the synthesis conditions of DQ-TBC complex. The results suggest that the electrooxidation of TBC in the presence of DES leads to DQ through an ECE mechanism. The synthesized compound showed promising antibacterial activity against Bacillus cereus and Staphylococcus aureus.
ELECTROCHIMICA ACTA
(2022)
Article
Chemistry, Analytical
Fahimeh Varmaghani, Vahid Nemati
Summary: The electrochemical oxidation of urazoles in the presence of various amines was studied, demonstrating competition between oxidative ring cleavage of urazoles, electrocatalytic oxidation of amines (EC' mechanism), and coupling reaction of amines and urazoles. The results showed that the oxidized form of urazole is unstable, especially when electron-withdrawing groups are present in the structure, leading to oxidative ring cleavage.
JOURNAL OF ELECTROANALYTICAL CHEMISTRY
(2022)
Article
Electrochemistry
Heydar Hameed Salman Arkwazee, Niloofar Mohamadighader, Davood Nematollahi, Arash Rabiee, Hojjat Alizadeh
Summary: This article describes a method for synthesizing new sulfonamide derivatives using electrochemical methods without toxic reagents, and finds that these products have good antibacterial performance against bacteria.
JOURNAL OF THE ELECTROCHEMICAL SOCIETY
(2022)
Article
Electrochemistry
Niloofar Mohamadighader, Davood Nematollahi, Mahnaz Saraei
Summary: Electrochemical oxidation of phenothiazine in an acetonitrile/water mixture was investigated, revealing that the oxidation pathway varies with respect to pH. The results led to the synthesis of two new types of PTZ dimer and provided insights into the oxidation mechanism of PTZ.
ELECTROCHIMICA ACTA
(2022)
Article
Chemistry, Multidisciplinary
Razzagh Rahimpoor, Ali Firoozichahak, Saber Alizadeh, Houman Serkan, Davood Nematollahi
Summary: This paper synthesized an aluminum-based metal-organic framework and utilized it in high-performance liquid chromatography for the reliable determination of cyclophosphamide in urine samples. By optimizing various parameters, satisfactory measurement results and recovery rates were obtained.
Article
Electrochemistry
Mohammad Reza Talebi, Davood Nematollahi, Ahmad Reza Massah
Summary: The electrochemical oxidation of N-(4-aminophenyl) and N-(4-hydroxyphenyl)benzenesulfonamide derivatives was investigated at different pH values and concentrations. The oxidation potential and mechanism of these compounds were found to be pH dependent. The oxidation products were found to undergo hydroxylation and/or dimerization reactions. The adsorption behavior and oxidation products under conditions similar to the human body were also studied.
ELECTROCHIMICA ACTA
(2023)
Article
Electrochemistry
Faezeh Zivari-Moshfegh, Fereshteh Javanmardi, Davood Nematollahi
Summary: The electrochemical behavior of rifampicin, an anti-tuberculosis drug, was studied in a water/ethanol mixture. The drug was found to undergo two-step oxidation, with the first step being a reversible oxidation of the hydroquinone moiety and the second step being an irreversible oxidation of the phenolic ring. The adsorption activity and diffusion coefficient of rifampicin were also determined, indicating that the first oxidation step is diffusion-controlled and the second step is a diffusion/adsorption control process. The oxidation of rifampicin was found to be complex and highly pH-dependent, with different rates of reaction observed for different drugs used in combination therapy.
ELECTROCHIMICA ACTA
(2023)
Article
Electrochemistry
Faezeh Zivari-Moshfegh, Davood Nematollahi
Summary: This study investigates the toxic metabolites formed from the oxidation of rifampicin and acetaminophen in the body. It provides strong evidence of a catalytic reaction between vitamin C and the oxidized form of rifampicin. Additionally, contrary to previous reports, this study discovers another catalytic reaction between oxidized acetaminophen and rifampicin.
JOURNAL OF THE ELECTROCHEMICAL SOCIETY
(2023)
Article
Electrochemistry
Zahra Godini, Davood Nematollahi, Faezeh Zivari-Moshfegh
Summary: In this study, the electrochemical complexation of five azole antifungal drugs with silver, copper and zinc cations was conducted in an undivided electrolytic cell. Twenty complexes were synthesized using a simple method in water/ethanol mixtures with high yield and purity. The applied current and acid concentration were found to have no significant effects on the yield and purity of the complexes, but they did affect the cell voltage and energy consumption.
JOURNAL OF THE ELECTROCHEMICAL SOCIETY
(2023)
Article
Multidisciplinary Sciences
Pouria Patoghi, Ali Sadatnabi, Davood Nematollahi
Summary: In this study, a new convergent paired electro-organic synthesis method for sulfonamide derivatives was introduced, which follows the principles of green chemistry and does not require catalysts, oxidants, halogens, or amines. Instead of using toxic amine compounds, an innovative mechanism based on the reduction of nitro compounds and in-situ production of amine compounds was used. The mechanism involves cathodic reduction of nitro compounds to hydroxylamine compounds and anodic oxidation of hydroxylamine compounds to nitroso compounds.
SCIENTIFIC REPORTS
(2023)
Article
Chemistry, Analytical
Nasim Shamsvand, Fahimeh Varmaghani, Babak Karimi, Hamzeh Hassanaki
Summary: The role of nitrogen functional groups in nitrogen-doped ordered mesoporous carbons (OMCs) was investigated using two home-made ionic liquid-derived OMCs with different nitrogen concentrations. It was found that the nitrogen content had a significant impact on the loading of electroactive species on the OMCs.
