Article
Chemistry, Multidisciplinary
Vyacheslav Morozov, Yurii Shklyaev
Summary: A method for rapidly constructing indolo[3,2-l]acridin-7-one systems bearing an isocryptolepine scaffold is described. The method involves a metal-free condensation reaction in concentrated sulfuric acid, resulting in the formation of polyannulated compounds with four new stereogenic centers in a highly diastereoselective manner. The reaction includes elecrophilic dearomatization of a methoxyarene, formation of a spirocyclic intermediate, and an intramolecular 1,4-nucleophilic addition sequence.
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, Inorganic & Nuclear
Harshal Dabhane, Suresh Ghotekar, Manohar Zate, Sagar Kute, Ghanshyam Jadhav, Vijay Medhane
Summary: Nanotechnology offers a method for synthesizing nanoparticles, while green plant extract synthesis methods have been successfully applied to overcome environmental issues. The study demonstrates a simple, efficient, inexpensive, and environmentally friendly approach to produce magnesium oxide nanoparticles.
INORGANIC CHEMISTRY COMMUNICATIONS
(2022)
Review
Chemistry, Applied
Yong-Xing Song, Da-Ming Du
Summary: The aza-Michael addition cascade reaction is an important synthetic method for constructing functionalized C-N bonds, widely used in the synthesis of chiral drugs, intermediates, and natural products. This review highlights recent developments in asymmetric synthesis, including various types of aza-Michael addition triggered cascade reactions, reaction mechanisms, and derivatization experiments.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Multidisciplinary
Dimitri Berne, Sebastien Lemouzy, Pascale Guiffrey, Sylvain Caillol, Vincent Ladmiral, Eric Manoury, Rinaldo Poli, Eric Leclerc
Summary: This study describes a spontaneous (uncatalyzed) Michael addition of thiols to alpha-trifluoromethyl acrylates and its efficient application in the preparation of a thermoset. Mechanistic investigation reveals a probable solvent-assisted proton transfer in the rate-determining step and a considerable lowering of the energy barrier induced by the CF3 group in the addition of arene- and alkanethiols to tert-butyl trifluoromethyl acrylate in polar aprotic solvents.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Organic
Dmitry Osipov, Kirill S. Korzhenko, Vitaly A. Osyanin
Summary: We investigated the reaction of 1H-azoles with precursors of ortho- and para-quinone methides of 3-hydroxypyridine series. The synthesis of hybrid heterocycles containing both pyridine and azole moieties was convenient and efficient. Two new heterocyclic systems were obtained through cascade aza-Michael/intramolecular nucleophilic substitution reactions.
Article
Chemistry, Organic
Sadhanendu Samanta, Jin Cui, Hidetoshi Noda, Takumi Watanabe, Masakatsu Shibasaki
Summary: In this study, a gram-scale syn-selective asymmetric vinylogous addition of butenolides to chromones was developed using an Al-Li-BINOL (ALB) complex catalyst. The reaction showed high diastereoselectivity with ratios up to 20:1 and enantioselectivity of 84-98% for various substrate combinations. This method is complementary to previous reports and improves selectivity for several chromones. Computational studies support the role of ALB as a bifunctional catalyst in this reaction and provide insights into the origin of the observed stereoselectivity.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Sadhanendu Samanta, Jin Cui, Hidetoshi Noda, Takumi Watanabe, Masakatsu Shibasaki
Summary: A gram-scale syn-selective asymmetric vinylogous addition of butenolides to chromones, catalyzed by an Al-Li-BINOL (ALB) complex, was developed in this study. The diastereoselectivity reached 20:1 with 84-98% ee for various combinations of substrates. This protocol complements previous methods and improves selectivity for multiple chromones.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Applied
Duraipandi Devi Priya, Selvaraj Mohana Roopan
Summary: A novel, flexible and strong technique for the synthesis of indazolo[3,2-b]quinazoline motifs using NiTiO3 as a catalyst was reported. The reaction pathway involved Claisen-Schmidt condensation, Michael reaction, and oxidation for three-component domino convention. The synthesized compounds exhibited fluorescent properties and high fluorescence quantum yields.
APPLIED ORGANOMETALLIC CHEMISTRY
(2021)
Article
Chemistry, Physical
Swayamsiddha Kar, Prashant Rai, Sai Manohar Chelli, Abdul Akhir, Naveen Shivalingegowda, Sidharth Chopra, Lokanath Neratur Krishnappagowda, Siva Kumar Belliraj, Nageswara Rao Golakoti
Summary: The unexpected spiro cyclic products were obtained from the alkali-catalyzed Claisen-Schmidt reaction of ketones with salicylaldehyde, in addition to the bis-chalcones. Under acid catalysis, the spiro products transformed into benzopyrylium salts. The study characterized the products obtained from cyclopentanone, cylcohexanone, and cylcoheptanone using various analytical techniques, and investigated the thermal properties of the spiro molecule synthesized from cylcoheptanone reactant. The impact of solvents, Lewis acid catalyst, and thermodynamic parameters like entropy were explored to rationalize the phenomenon, as well as the relationship between the bis-chalcone, spiro molecule, and benzopyrylium salt, with the investigation of ring expansion from cyclopentanone to cycloheptanone. The antibacterial potential of the synthesized spirobibenzopyrans and benzopyrylium salts was also presented.
JOURNAL OF MOLECULAR STRUCTURE
(2021)
Article
Chemistry, Physical
Na Liu, Xinyue Zhou, Li Zhou, Zongquan Wu
Summary: A novel diazoacetate monomer was successfully synthesized, leading to the formation of helical polycarbenes with well-defined molecular weights and low polydispersity. These polycarbenes showed high catalytic ability in asymmetric Michael addition reactions, with increased enantioselectivity and diastereoselectivity compared to traditional catalysts. Additionally, the helical polycarbene catalyst can be easily recovered and reused multiple times without significant loss of its selectivity.
Article
Crystallography
Marco A. Obregon-Mendoza, Imilla I. Arias-Olguin, William Meza-Morales, Yair Alvarez-Ricardo, Maria Isabel Chavez, Ruben A. Toscano, Julia Cassani, Raul G. Enriquez
Summary: Expected (E)-but-3-en-2-ones and unexpected 3-methylcyclohex-2-enones were synthesized via Claisen-Schmidt reaction, showing their configuration and conformational characteristics. Compound III presents a rare case of racemic solid solution, where crystal packing is mainly stabilized by weak intermolecular interactions.
Article
Chemistry, Multidisciplinary
Carlos Andres Coy-Barrera, Inti Camilo Monge, Diego Quiroga
Summary: In this study, a series of chalcone analogs were synthesized and tested as corrosion inhibitors for carbon steel in HCl solutions. Three chalcone compounds (CH11, CH15, and CH16) showed significant anticorrosive activity with increasing mass. Theoretical calculations using DFT were performed to explain the mechanism of corrosion inhibition by these compounds.
ARABIAN JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Applied
A. Petrova, E. F. Khusnutdinova, A. N. Lobov, L. M. Zakirova, N. T. T. Ha, D. A. Babkov
Summary: In this study, a series of 24-ethylcholest-4-ene-3,6-dione 2E-arylidene derivatives were synthesized from a natural phytosterol beta-sitosterol by Claisen-Schmidt reaction. The obtained compounds were characterized by NMR spectroscopy and evaluated for their cytotoxicity and alpha-glucosidase inhibitory activity. Compound 3 showed selective cytotoxic effect against U251 cancer cell line, while compounds with pyridin-4ylmethylene and furan-2-ylmethylene-5 fragments exhibited the most potent alpha-glucosidase inhibitory activity.
NATURAL PRODUCT RESEARCH
(2022)
Article
Chemistry, Physical
Samiran Bhattacharjee, Aftab Ali Shaikh, Wha-Seung Ahn
Summary: CuBTC was found to be an effective heterogeneous catalyst for the aza-Michael addition reaction of various amines to electron deficient alkenes at room temperature, providing high product yields and selectivity. While cyclic and aliphatic amines showed high yields within a short reaction time, aromatic amines exhibited slower reaction rates and lower yields. The catalyst could be reused multiple times without losing activity, and XRD and SEM analysis confirmed the retention of catalyst crystallinity during the reaction.
Article
Biochemistry & Molecular Biology
Wenliang Song, Yu Zhang, Deng-Guang Yu, Chinh Hoang Tran, Menglong Wang, Anuraj Varyambath, Jisu Kim, Il Kim
Summary: This study presents an efficient and systematic approach to synthesize bioapplicable porous hollow polymeric capsules, offering potential applications in drug delivery. By converting hydroxyl groups on the surface to carboxyl groups, biomolecules can be covalently decorated on the organic capsules. The research results show that these organic capsules have potential applications in drug encapsulation efficiency and release.
Article
Chemistry, Applied
Anuraj Varyambath, Wen Liang Song, Saurabh Singh, Ji Su Kim, Il Kim
Summary: In this study, the morphology and porosity design of biphenyl-based hyper-cross-linked porous organic polymers were demonstrated using a Lewis acid catalyzed Friedel-Crafts polymerization with FDA as cross-linker. By varying the monomer to FDA ratio, diverse morphologies such as nanospheres, nanofibers, and flower-like nanostructures were achieved, leading to outstanding adsorption capacity towards pollutants and excellent electrochemical performance for energy storage applications.
MICROPOROUS AND MESOPOROUS MATERIALS
(2021)
Article
Polymer Science
Su Hyeon Jeon, Jae Eon Jeong, Seongkyun Kim, Sungwan Jeon, Jin Woo Choung, Il Kim
Summary: A series of poly(ether ester) elastomers are synthesized to develop new materials for automobile weather-stripping and seal parts, replacing conventional rubbers. Hardness can be modulated by controlling chain extender composition and the ratio of hard to soft segments, while crystallinity and phase separation behavior can also be tuned accordingly.
Article
Chemistry, Multidisciplinary
Sirigireddy Sudharsan Reddy, Anuraj Varyambath, Reddi Mohan Naidu Kalla, Wenliang Song, Il Kim
Summary: In this study, a library of 3-indole substituted sulfonyl 4H-chromenes was successfully built using recyclable and metal-free heterogeneous base catalysts. The synthesized cPOP microspheres exhibited excellent catalytic activity for a variety of substrates under mild reaction conditions, with the catalysts being recyclable up to six cycles without leeching and deactivation. This approach represents a green synthesis method with minimal solvent usage and simplified product workup procedures, adhering to the principles of green chemistry.
Article
Polymer Science
Rimesh Augustine, Saji Uthaman, Nagendra Kalva, Kuen Hee Eom, Kang Moo Huh, Shameer Pillarisetti, In-Kyu Park, Il Kim
Summary: A series of novel synthetic polymer polypeptide bio-conjugates have been synthesized for enhanced chemo-photothermal therapy, showing potential therapeutic effects on colon cancer cells through successful drug encapsulation and release.
Article
Polymer Science
Kuen Hee Eom, Shuwei Li, Eun Gyeong Lee, Jae Ho Kim, Jung Rae Kim, Il Kim
Summary: Cell-penetrating peptides are facilitated by the presence of arginine or other guanidinium groups. However, little research has been done on the impact of these functional groups on antimicrobial peptides. In this study, a series of cationic linear, star, and multi-branched copolymers were synthesized and their antibacterial efficacy was tested. The results showed that the structure and composition of the copolymers significantly influenced their antibacterial activity, with the multi-branched structure exhibiting the highest efficacy.
Review
Biochemistry & Molecular Biology
Yu Zhang, Wenliang Song, Yiming Lu, Yixin Xu, Changping Wang, Deng-Guang Yu, Il Kim
Summary: This work discusses the research progress and applications of poly(alpha-L-glutamic acid) (PGA) and its nanomaterials in drug delivery. It is found that PGA has biocompatibility and biodegradability, making it a promising candidate for drug delivery systems.
Article
Polymer Science
Chinh-Hoang Tran, Min-Woong Lee, Soo-Jeong Lee, Jin-Hyeok Choi, Eun-Gyeong Lee, Ha-Kyung Choi, Il Kim
Summary: A series of heterogeneous Zn-Co double metal cyanide (DMC) catalysts were investigated for ring-opening polymerization (ROP) of various cyclic monomers. It was found that inexpensive and commonly used organic solvents were effective complexing agents for the preparation of DMC catalysts, which showed high catalytic activity for the ROP of propylene oxide, epsilon-caprolactone, and delta-valerolactone. The chemical structures and compositions of the catalysts were determined using various techniques, and alpha, omega-hydroxyl-functionalized polyether and polyester polyols with high yields and tunable molecular weights were successfully synthesized in the presence of different initiators. Kinetic studies of the ROP of delta-valerolactone were also conducted to confirm the reaction mechanism.
Article
Polymer Science
Huining Ding, Xianmin Wu, Bing Han, Kening Guo, Zhongyu Duan, Binyuan Liu, Il Kim
Summary: Upcycling through catalytic depolymerization is an attractive form of chemical recycling that allows for large-scale valorization of plastic wastes. In this study, a model polyester/polycarbonate block copolymer was successfully depolymerized using an organocatalytic system, resulting in both degradation and configurational transformation. The degradation process occurred in three distinct steps and the stereochemical transformation of the polymer block was observed throughout the degradation stage. The findings suggest that the depolymerization and configurational transformation can be controlled by adjusting the depolymerization atmosphere.
POLYMER DEGRADATION AND STABILITY
(2022)
Article
Chemistry, Multidisciplinary
W. Song, M. Zhang, X. Huang, B. Chen, Y. Ding, Y. Zhang, D. G. Yu, I. Kim
Summary: A processible porous polymer with swellable hollow spherical morphology and branched L-borneol antibacterial agents was reported, which possesses high adsorption abilities and antibacterial performance. It can be prepared as a fine powder, anchored on membranes, processed into tablets, and assembled as a dye absorption device, showing notable potential as adsorbents for water purification and sewage treatment.
MATERIALS TODAY CHEMISTRY
(2022)
Review
Polymer Science
Wenliang Song, Yu Zhang, Chinh Hoang Tran, Ha Kyung Choi, Deng-Guang Yu, Il Kim
Summary: Porous organic polymers (POPs) and their derivatives have diverse applications in catalysis, absorption, separation, sensing, biomedical engineering, and energy storage/conversion. The controlled synthesis of morphologically defined POPs offers an effective route to prepare novel nanomaterials with broad application scope. This review summarizes the recent research progress in the development of morphologically controlled POPs and highlights the relationship between morphology and performance.
PROGRESS IN POLYMER SCIENCE
(2023)
Article
Polymer Science
Jin-Hyeok Choi, Jeong-Jae Woo, Il Kim
Summary: Researchers synthesized α,ω-hydroxyl-terminated polycaprolactone (PCL) polyols and used them as soft segments to produce thermoplastic poly(ester ester) elastomers. Compared to conventional thermoplastic poly(ether ester) elastomers, the PCL-based TPEs exhibited superior mechanical properties and biodegradability. This study demonstrates significant potential for producing biodegradable TPEs with better properties than polyether-derived elastomers.
Article
Chemistry, Multidisciplinary
Chinh Hoang Tran, Ha-Kyung Choi, Eun-Gyeong Lee, Byeong-Ryeol Moon, Wenliang Song, Il Kim
Summary: A series of Prussian blue analogs (PBAs) were investigated as heterogeneous catalysts for the fixation of carbon dioxide (CO2) to glycidol. Zn(II)-Co(III) PBA with a cubic crystal structure exhibited the highest catalytic activity, selectivity, and recyclability for the cycloaddition reaction. By using a Zn(II)-Co(III) double metal cyanide catalyst, branched polycarbonate polyols and linear polycarbonates with high carbonate content were produced via ring-opening copolymerization of CO2 and various epoxides. Mechanistic pathways were proposed combining experimental results with computational studies.
JOURNAL OF CO2 UTILIZATION
(2023)
Article
Polymer Science
Xiao Zhang, Jincheng Dong, Yun Su, Eun Gyeong Lee, Zhongyu Duan, Il Kim, Binyuan Liu
Summary: An oligo(carbonate-ether) triol with controllable molecular weight and tunable carbonate unit content has been synthesized through copolymerization of propylene oxide and CO2 using a zinc-cobalt double metal cyanide catalyst. The highest catalytic activities achieved are 4.37 kg/g and 5.38 kg/g for oligo(carbonate-ether) triol and oligopolyether triol, respectively. The synthesis also yields the lowest level of cyclic propylene carbonate byproduct reported for branched polyols. NMR and ESI-MS analyses reveal three distinct growth stages of the multi-arm polymers. This work provides an efficient pathway for CO2 fixation into multi-arm polycarbonate polyols.
Review
Materials Science, Biomaterials
Yunxin Tang, Anuraj Varyambath, Yuanchen Ding, Bailiang Chen, Xinyi Huang, Yu Zhang, Deng-guang Yu, Il Kim, Wenliang Song
Summary: Porous organic polymers have attracted considerable attention due to their hierarchical pore structures, variable morphologies, and tunable biological properties. This review discusses the synthetic and post forming/control methods for controlling the hierarchical structures and morphologies of porous organic polymers, highlighting the different methods that affect their specific surface areas, hierarchical structures, and unique morphologies. Additionally, the applications of porous organic polymers in drug encapsulation and the development of stimuli-responsive materials are explored, focusing on their use for targeted drug release and as therapeutic agents.
BIOMATERIALS SCIENCE
(2022)
