Article
Chemistry, Organic
Yan Jiang, Hao-Jie Ma, Xue-Long Wang, Yi Yang
Summary: A Yb(OTf)(3)-catalyzed formal (4 + 3) cycloaddition reaction was successfully achieved using donor-acceptor cyclopropanes and 3-benzylideneindoline-2-thiones as reactants. Functionalized 5,10-dihydro-2H-thiepino[2,3-b]indole derivatives were synthesized with good yields and moderate to good diastereoselectivity. This reaction represents the first (4 + 3) cycloaddition of 3-benzylideneindoline-2-thiones.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Jianwei Yan, Linxia Zheng, Jiangfei Wang, Xiaomin Liu, Youhong Hu
Summary: A mild oxidative sequential tandem reaction was developed for the rapid synthesis of diverse 2-aryl-3-(2-aminoaryl) quinoxalines. This method utilized 2-substituted indoles as substrates to form quinoxalines in a one-pot reaction. The key step in this tandem reaction was the formation of 3-iodoindoles, which were oxidized with DMSO to generate active imine 2-substitued 3H-indol-3-ones. The active imines were then captured in situ by 1,2-diaminobenzenes to construct diverse quinoxalines. This transformation could be conducted at room temperature and exhibited excellent tolerance towards various functional groups.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Yan Jiang, Hao-Jie Ma, Xue-Long Wang, Yi Yang
Summary: A new compound was synthesized successfully in this study by using Yb-(OTf)(3) catalyst to react donor-acceptor cyclopropanes with sulfur-containing 4π components. The reaction showed high yields and moderate to good diastereoselectivity.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Applied
Junmin Sun, Hai Cheng, Yao Zhang, Yinmin Zhang, Xunfeng Lan, Yongfeng Zhang, Qineng Xia, Daqian Ding
Summary: This study presents the selective catalytic conversion of biomass-derived humins into cyclic hydrocarbons using a Ru/W-P-Si-O catalyst, achieving high conversion rates and selectivity. Results showed that the CAC bond network can be efficiently depolymerized at mild reaction temperatures, resulting in up to 95.4% conversion of humins with 88.3% yield of cyclic hydrocarbons. The research paves the way for the efficient production of cyclic and aromatic hydrocarbons from humin polymer through Lewis acid-catalyzed Diels-Alder reactions.
JOURNAL OF ENERGY CHEMISTRY
(2021)
Article
Chemistry, Physical
Chaymae Bourhou, Hind Benouda, Reda Bellaouchi, Mohammed Merzouki, Elmehdi Fraj, Tarik Harit, Allal Challioui, Abdeslam Asehraou, Rachid Touzani, Ismail Ozdemir, Boufelja Bouammali
Summary: This study involves the synthesis of novel Bis(arylidene-2-[(tetrazol-5-yl)]alkane derivatives and their evaluation for antibacterial and antifungal activities. The compounds showed moderate yields and their structures were determined through spectroscopic analyses. In vitro testing revealed antimicrobial properties against various bacterial and fungal strains. Docking study further confirmed the interactions of the compounds with the active site in Staphylococcus aureus.
JOURNAL OF MOLECULAR STRUCTURE
(2023)
Article
Chemistry, Inorganic & Nuclear
Clarence Tan, Hendrik Tinnermann, Simon Sung, Li Heng Kat, Rowan D. Young
Summary: This report discusses the synthesis and characterization of a series of symmetric and asymmetric PCcarbeneP pincer complexes through a proligand dehydration approach. The study found that introducing sterically encumbering aryl substituents at the pincer phosphino positions can impart selectivity to the complexes.
Article
Chemistry, Organic
Aleksandras Lotuzas, Anton El Khoury, Liubo Li, Patrick G. Harran
Summary: 4-Isocyanobut-1-ene reacted rapidly with acetyl bromide to form an unstable imidoyl bromide adduct. By subsequent in situ cyclization under Heck conditions, a stable prototropic isomer of 2-acetyl-3-methylpyrrole was obtained. The reactivity of this molecule towards acids, bases, and oxidants was investigated, and its conversion into an alpha-methylidene gamma-lactam was demonstrated. In its protonated form, the molecule functioned as a reactive dienophile in Diels-Alder reactions.
Article
Chemistry, Applied
Fabio Wilbert, Thomas J. J. Muller
Summary: One-pot syntheses of 3,3-diarylallylidene indolinones were achieved by pseudo-four-and pseudo-five-component reactions. The title compounds, which are a mixture of E/Z-configured isomers, were assessed for their photophysical characteristics using absorption and solid-state emission spectroscopy. The fluorescence of 3,3-diarylallylidene indolinones in the solid state was observed regardless of their configuration, but only when electron-withdrawing and weakly electron-releasing remote p-phenyl substituted dyes were present with concomitant Boc substitution of the lactam moiety. DFT and TD-DFT calculations were used to reproduce and rationalize the electronic structure of the longest wavelength absorption and emission bands.
Article
Chemistry, Organic
Arunan Palanimuthu, Chinpiao Chen, Gene-Hsian Lee
Summary: A diastereoselective aza-Diels-Alder reaction has been developed between in situ generated 2-aminophenyl-substituted enones and alpha-cyano-alpha,beta-unsaturated aromatic ketone. Highly substituted tetrahydroquinolines with an all-carbon quaternary center were prepared as both exo and endo isomers with excellent diastereoselectivity and high yields under very mild conditions.
TETRAHEDRON LETTERS
(2021)
Article
Chemistry, Physical
Tao Wang, Jie Li, Hanwen Yan, Guoliang Zhang, Shifeng Li
Summary: In this study, a series of secondary amines/acids were explored as catalysts for the synthesis of methacrolein (MAL) from formaldehyde and propionaldehyde. The structure of the amines and acids directly affected the yield of MAL. The catalytic performance of the system was systematically studied and optimized.
Review
Chemistry, Inorganic & Nuclear
Amir Mohammad Ghadiri, Mehran Farhang, Parya Hassani, Atena Salek, Ali Talesh Ramezani, Ali Reza Akbarzadeh
Summary: Carbon-carbon cross-coupling reactions, such as the Heck and Suzuki reactions, are widely used in organic and inorganic chemistry. The choice of catalyst is critical in these reactions, and various catalysts such as nanoparticles and metalloporphyrins have been investigated. This review focuses on the use of metalloporphyrin catalysts in the Heck and Suzuki reactions, discussing their impact on different porphyrin substrates. The advantages of porphyrins, such as non-toxicity and flexibility, make them a suitable catalyst for these reactions.
INORGANIC CHEMISTRY COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Bo-Wei Huang, Jeng-Liang Han
Summary: A vinylogous addition reaction of allyl aryl ketones can be catalyzed by squaramide catalysts to give good yields and excellent regioselectivity. Chiral tertiary alcohols and bicyclic pyrrolidones can be synthesized in good to excellent yields, enantioselectivities, and diaseteroselectivities. Experimental and DFT calculations suggest that the reaction favors 1,2-addition at lower temperatures and 1,4-addition/cyclization at higher temperatures. Compound 4 may form through either the 1,4-addition/cyclization pathway or retro-aldol reaction of compound 3, followed by subsequent 1,4-addition/cyclization.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Shuangshuang Zhao, Kuiliang Li, Xiang Sun, Zhenggen Zha, Zhiyong Wang
Summary: In this study, an asymmetric [4 + 2] cycloaddition reaction of β,γ-unsaturated α-keto esters with 2-vinylpyrroles was developed in water using a low-loading copper complex catalyst. Optically pure 3,4-dihydro-2H-pyran derivatives were obtained in excellent yields, with high diastereoselectivities and enantioselectivities. The proposed mechanism was supported by DFT calculations.
Article
Chemistry, Organic
Qi Xue, Ren Wang, Wen-Yu Zhang, Fang-Fang Shen, Yang Li, Qing Sun, Jin-Heng Li
Summary: A new palladium-catalyzed multicomponent dearomatization of arylamines with CO and propargylic acetates for the synthesis of bridged polycyclic lactams is reported. This method enables double annulation at the ipso and para positions of the amino group, leading to the formation of four new bonds, including three C-C bonds and one C-N bond. DFT calculations and experimental studies suggest that the efficient formation of the allenecarboxanilide intermediate is crucial for the dearomative transformation.
Article
Chemistry, Organic
Man Ki Sit, Hui Hui Cao, Yan-Dong Wu, Tsz Chun Yip, Lars Eric Bendel, Wen Zhang, Wei-Min Dai
Summary: The synthesis of C19-truncated maltepolide E was achieved using a diene-ene ring-closing metathesis strategy, while preserving the integrity of the C11-C14 alkenyl epoxy unit. Removal of the C17-OH group resulted in its attack at the C14 position, causing double bond migration and epoxide ring opening to produce C19-truncated maltepolides A and B, which are proposed intermediates in the biosynthesis of maltepolides.
Article
Biophysics
Willy Carrasquel-Ursulaez, Mahzad Dehghany, Corey L. Jones, Vinaykumar Idikuda, Brian Lu, Jennifer M. Schomaker, Baron Chanda
Summary: In this study, two new families of benzo(crown-ether) compounds, termed monoacylated and monoalkylated benzo(crown-ethers) (MABCE), were synthesized and characterized. These compounds can inhibit bacterial growth and transport ions across biological membranes. The results show that the preference of these compounds for specific ions is not achieved through ion-selective transport, but rather through the regulation of assembly of ion-conducting supramolecular complexes or its membrane insertion by cations. Additionally, the formation of these assemblies in the membrane does not require hydrogen bonding network.
BIOPHYSICAL JOURNAL
(2022)
Article
Engineering, Chemical
Ghazaleh Jahani, Masoume Malmir, Majid M. Heravi
Summary: A novel nitrogen- and sulfur-doped graphene carbon dot-modified magnetic nanocomposite was synthesized and characterized. The catalyst, Fe3O4/g-CSNCDs, showed excellent catalytic activity and selectivity in alcohol oxidation. The carbonation of reagents and magnetic nanoparticles were found to have an impact on the catalytic performance. The Fe3O4/g-CSNCDs catalyst not only exhibited recyclability and magnetic recovery, but also showed improved catalytic activity compared to the bare g-CSNCDs.
INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH
(2022)
Review
Chemistry, Multidisciplinary
Heshmatollah Sepahvand, Majid M. Heravi, Mahyar Saber, Seyyed Emad Hooshmand
Summary: Enzymes play a key role in chemical industries as biological catalysts. Immobilization of enzymes using techniques like the Ugi multicomponent reaction can enhance their stability and activity, leading to a more robust catalyst system. Immobilized enzymes through Ugi MCR show good stability and activity, with the potential for synergistic effects on enzyme activities.
JOURNAL OF THE IRANIAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Multidisciplinary
Majid M. Heravi, Reihaneh Malakooti, Kosar Kafshdarzadeh, Zahra Amiri, Vahideh Zadsirjan, Hassan Atashin
Summary: An eco-friendly method for the synthesis of substituted dihydropyrano[2,3-c]pyrazole and benzylpyrazolyl coumarin derivatives has been developed through a multicomponent reaction. The method offers wide scope, high yields, short reaction times, and simple workup procedure. Furthermore, the nanocatalyst used in this method can be easily recovered and reused multiple times without significant loss in catalytic activity and performance.
RESEARCH ON CHEMICAL INTERMEDIATES
(2022)
Article
Chemistry, Organic
Zahra Khademi, Majid M. Heravi
Summary: The Claisen condensation is a base-mediated reaction that generates alpha,beta-keto ester by reacting an ester with a molecule containing alpha-hydrogen atom. This review focuses on the applications of Claisen condensation in the total synthesis of natural products, covering relevant literature up to the beginning of 2021.
Article
Multidisciplinary Sciences
Samahe Sadjadi, Fatemeh Koohestani, Majid M. Heravi
Summary: 1-Butyl-3-vinylimidazolium chloride was synthesized and polymerized with acrylamide to form an ionic liquid-containing polymer, which was then used to create a composite with iron-based metal-organic framework. The resulting composite exhibited high catalytic activity and recyclability for ultrasonic-assisted Knoevenagel condensation.
SCIENTIFIC REPORTS
(2022)
Review
Chemistry, Multidisciplinary
Majid M. Heravi, Vahideh Zadsirjan
Summary: This review summarizes recent advances in the synthesis and aromatization of Hantzsch 1,4-dihydropyridines under microwave irradiation, highlighting the use of this green approach.
Review
Chemistry, Applied
Yalda Rangraz, Majid M. Heravi
Summary: The development of methodologies for carbon-nitrogen bond formation is crucial in organic synthesis, as the resulting products are widely used in pharmaceuticals, biologically active compounds, and natural products. Recently, nanosized metal catalysts have gained significant attention for their excellent catalytic performance, high product yields, mild reaction conditions, and environmental sustainability. This review provides an overview of the latest progress in the fabrication of nanocatalysts and their applications in constructing carbon-nitrogen bonds via cross-coupling reactions.
APPLIED ORGANOMETALLIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Leyla Mohammadkhani, Majid M. Heravi, Farhad Panahi
Summary: This paper reports the efficient conversion of nitroarenes to anilines using immobilized palladium nanoparticles on a silica-starch substrate. The catalyst system exhibited high efficiency and could be reused multiple times.
MONATSHEFTE FUR CHEMIE
(2022)
Review
Chemistry, Organic
Majid M. Heravi, Batoul Alipour, Vahideh Zadsirjan, Masoume Malmir
Summary: The Robinson annulation is a significant reaction for the synthesis of alpha,beta-unsaturated ketone ring that involves the generation of two C-C bonds. It has been frequently used in the total synthesis of biologically active natural products. These products and their derivatives play a major role in pharmacotherapy, especially for cancer and infectious diseases.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Physical
Masoume Malmir, Majid M. Heravi, Zahra Yekke-Ghasemi, Satar Saberi, Masoud Mirzaei
Summary: A new heterogeneous catalyst, TBA8[Zr(W5O18)2]middot17H2O (Zr(W5)2), was synthesized and characterized. It was found that the catalyst had a sandwich-type structure consisting of zirconium ions and mono-lacunary Lindqvist [W5O18 ]4- anions, encapsulated by TBA+ cations. This catalyst exhibited hydrophobic properties and improved catalytic efficiency by trapping reactants on its surface. Using Zr(W5)2 as a catalyst, a series of 1,5-benzodiazepines were successfully synthesized via mild and solvent-free reactions.
JOURNAL OF MOLECULAR STRUCTURE
(2023)
Article
Chemistry, Applied
Masoume Malmir, Majid M. Heravi, Ghazaleh Jahani
Summary: Metal-organic frameworks (MOFs) are viable and environmentally friendly alternatives to traditional catalysts, and the magnetic Ox-CN-Cu-MOF catalyst has shown remarkable catalytic performance due to its unique structure and Lewis acidic properties. It also exhibits excellent recyclability.
APPLIED ORGANOMETALLIC CHEMISTRY
(2023)
Article
Biotechnology & Applied Microbiology
Masoumeh Bagheri Bisafar, Masoume Malmir, Majid M. Heravi
Summary: In this study, a novel magnetic MOFs-based catalyst was synthesized and showed good catalytic activity and stability for the reduction of nitroarenes and organic dyes. The catalyst can be easily separated and recovered by magnetic separation, and it can be reused for multiple cycles.
JOURNAL OF CHEMICAL TECHNOLOGY AND BIOTECHNOLOGY
(2023)
Article
Multidisciplinary Sciences
Zahra Yekke-Ghasemi, Majid M. Heravi, Masoume Malmir, Masoud Mirzaei
Summary: In this study, a tri-component composite Zr/SiW12/GO was prepared using an ultrasonic-assisted method. This composite, acting as a remarkable heterogeneous catalyst, showed exceptional catalytic performance in the oxidation reaction of sulfides to sulfoxides. The composite also demonstrated exceptional stability and could be reused up to four times without significant loss in its catalytic activity.
SCIENTIFIC REPORTS
(2023)
Review
Chemistry, Multidisciplinary
Majid M. Heravi, Vahideh Zadsirjan
Summary: The Hantzsch reaction is a well-known multi-component reaction for synthesizing 1,4-dihydropyridines, and microwave irradiation has been successfully utilized as a green energy source to promote this organic transformation. Literature survey shows that construction and aromatization of 1,4-DHPs can be effectively carried out under microwave irradiation in solution or dry media.
Article
Chemistry, Organic
Fuying Zhu, Yamei Lin
Summary: In this study, a low-metal iron-supported catalyst (Fe20/NC-Mg) was reported for the efficient synthesis of quinoxaline compounds, using water as a solvent and without additional bases. The synergistic effect of FeNx site and Mg (OH)2 nanorods in the catalyst played a key role in achieving high yields (82-91%) in 16 examples. The gram-level synthesis and reusability of the catalysts after four cycles demonstrated its industrial application potential.
Article
Chemistry, Organic
Mikhail Kozlov, Alexey Tyurin, Andrey Dmitrenok, Vyacheslav Rusak, Aleksander Fedorov, Igor Zavarzin, Yulia Volkova
Summary: This study presents a novel and practical synthesis method for phosphorus-substituted 1,3,4-thiadiazolines using phosphorylthioformic acid hydrazides and ketones. The protocol demonstrates operational simplicity, availability of reagents, and tolerance towards different functional groups.
Article
Chemistry, Organic
Jisna Jose, Thomas Mathew
Summary: 2-Cyclopentenone and its derivatives are highly esteemed synthetic intermediates with exceptional utility in organic synthesis. They are favored structural motifs in numerous pharmaceutical drugs and natural products, highlighting their significance. The review discusses the various methods used to synthesize cyclopentenones from 2016 to 2023.
