Review
Chemistry, Multidisciplinary
Luiz S. Longo, Fernanda A. Siqueira, Nicolas S. Anjos, Gabriela F. D. Santos
Summary: This review summarizes the recent progress on the use of scandium(III) triflate as a Lewis acid catalyst for multicomponent reactions in the synthesis of nitrogen-containing heterocycles, which are valuable privileged scaffolds in Organic and Medicinal Chemistry.
Article
Chemistry, Multidisciplinary
Weidong Jia, Jingjing Wang, Chengxi Wei, Ming Bian, Shuyin Bao, Lijun Yu
Summary: A new series of quinoxalinone derivatives were designed and evaluated for their hypoglycemic activity. Compounds 5i and 6b showed stronger hypoglycemic effects compared to the lead compounds and were comparable to the positive control Pioglitazone. They exerted hypoglycemic effects by alleviating cellular oxidative stress and modulating the interactions among GLUT4, SGLT2, and GLUT1 proteins. Compound 6b showed better cellular oxidative stress alleviation and binding for most of the screening targets compared to 5i. Overall, compound 6b is a potential lead compound with hypoglycemic activity.
FRONTIERS IN CHEMISTRY
(2023)
Article
Chemistry, Organic
Rui Zhao, Ling Wu, Si-Wei Chen, Zhen Cui, Xu-Hua Hu, Hui-Ru Yang, Hongfei Ye, Chun-Bao Miao, Xun-Xiang Guo
Summary: A cobalt-catalyzed method for the synthesis of quinoxalines using o-phenylenediamines and internal alkynes has been developed. This method provides a variety of quinoxalines in good to high yields under simple and mild reaction conditions, using molecular O-2 as a terminal oxidant. Preliminary mechanistic studies reveal a novel reaction mechanism different from the previously reported oxidation of alkynes to dicarbonyl compounds.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Xuemei Tang, Qing Zhou, Wenliang Zhan, Die Hu, Ran Zhou, Nan Sun, Shuai Chen, Wenneng Wu, Wei Xue
Summary: A series of quinoxaline derivatives were designed, synthesized, and evaluated for their antimicrobial activity against plant pathogenic bacteria and fungi. Some compounds exhibited significant antibacterial and antifungal activities in vitro, with compound 5j showing the most potent anti-Rhizoctonia solani activity and effectively controlling rice sheath blight in vivo.
Article
Chemistry, Organic
Chunlei Wu, Jian Liu, Du Kui, Yu Lemao, Xu Yingjie, Xiang Luo, Xi Meiyang, Runpu Shen
Summary: This study presents a simple and efficient method for the synthesis of spirooxindole derivatives. The method involves a three-component reaction of isatin, 5-aminopyrazole, and 1,3-dicarbonyl compounds (or beta-oxo-benzenepropanenitrile), catalyzed by copper triflate in ethanol. The advantages of this method are high efficiency, mild reaction conditions, recoverable catalyst, and environmentally friendly conditions.
POLYCYCLIC AROMATIC COMPOUNDS
(2022)
Article
Chemistry, Inorganic & Nuclear
Alexander C. Saunders, Coleman R. Burch, Christian R. Goldsmith
Summary: Gallium(III) salts, particularly GaCl3, can act as mild catalysts for the deformylation of aldehydes to alkenes by H2O2 and base, showing that redox-active transition metals are not strictly necessary for this reactivity. The identity of the counteranion and solvent strongly affects the activity and side-product formation. Although the catalysis is currently modest, with turnovers occurring quickly and with fewer side-products compared to transition metal peroxo complexes.
INORGANICA CHIMICA ACTA
(2022)
Article
Chemistry, Organic
Aleksandra Zasada, Jakub Brzeskiewicz, Damian Antoniak, Malgorzata Bechcicka, Rafal Loska, Mieczyslaw Makosza
Summary: The electrophilic nature of quinoxaline was studied in the vicarious nucleophilic substitution (VNS) of hydrogen, and it was found that only poorly stabilized nitrile carbanions were suitable for the VNS reactions, aiming to develop a general method for functionalizing the heterocyclic ring. 2-Chloroquinoxaline exhibited preferential SNAr reaction with chlorine as the substituent. Quinoxaline N-oxide was used in VNS reactions to prepare a variety of quinoxaline derivatives containing cyanoalkyl, sulfonylalkyl, benzyl, or ester substituents.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Qi Liang, Long Lin, Guodong Li, Xianqiang Kong, Bo Xu
Summary: A copper-catalyzed radical cyclization method was developed for the synthesis of cyanoalkyl-substituted phenanthridines and quinoxalines, showing excellent isolated yields. The reactions proceed under mild conditions, exhibit a broad substrate scope, and have excellent functional group tolerance.
CHINESE JOURNAL OF CHEMISTRY
(2021)
Article
Chemistry, Organic
Akanksha M. Pandey, Shankhajit Mondal, Boopathy Gnanaprakasam
Summary: Continuous-flow reactors are an ideal tool for synthesizing potentially explosive but synthetically useful organic substances. This study reports the continuous-flow direct azidation of alcohols using TMSN3 as a transfer reagent and Amberlyst-15 as a recyclable catalyst. The study also explores the application of continuous-flow reactors in other organic reactions.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
John J. Monteith, Katerina Scotchburn, L. Reginald Mills, Sophie A. L. Rousseaux
Summary: A Ni-catalyzed cross-coupling reaction has been developed for the synthesis of thiocarboxylic acid derivatives using readily accessible O-alkyl xanthate esters or thiocarbonyl imidazolides and organozinc reagents. This method offers advantages such as fast reaction time, mild reaction conditions, and ease of starting material synthesis, providing a useful complementary approach for accessing a diverse range of thiocarbonyl-containing compounds compared to previously established methodologies.
Article
Chemistry, Organic
Zhenke Yang, Jidan Liu, Yuting Li, Jiawen Ding, Liyao Zheng, Zhao-Qing Liu
Summary: A one-pot three-component synthesis method for the preparation of multifunctionalized isoquinolones via Rh(III)-catalyzed C-H activation and tandem annulation has been developed. The catalytic system shows readily available starting materials, a wide tolerance of functional groups, a short reaction time, and high yields. The synthetic utility of the reaction is demonstrated by gram-scale synthesis and derivatization of the obtained products.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Zhenke Yang, Jidan Liu, Yuting Li, Jiawen Ding, Liyao Zheng, Zhao-Qing Liu
Summary: The one-pot three-component synthesis of multifunctionalized isoquinolones using Rh(III)-catalyzed oxazolinyl-directed C-H activation and tandem annulation has shown great potential due to its readily available starting materials, wide tolerance of functional groups, short reaction time, and high yields. The synthetic utility of the cascade reaction was further demonstrated by gram-scale synthesis and derivatization of the obtained products.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Sanjeev Kumar, Saiprasad Nunewar, Tharun Kumar Sabbi, Vinaykumar Kanchupalli
Summary: Here, we report the Rh(III)-catalyzed C-H activation followed by redox-neutral [3 + 2] annulation of sulfoxonium ylides with 1,3-diynes, delivering alkynated indenone derivatives. This method shows a broad substrate scope, good functional group tolerance, and mild reaction conditions.
Article
Chemistry, Organic
Qiuyu Zhu, Yu Tang, Biao Yu
Summary: A catalytic glycosyl fluoride activation system using the GeCl2·dioxane-AgBF4 combination was developed, involving reversible activation of C-F bond and reversible chloride ion transfer. This system is easy to operate, proceeds at room temperature, and has a broad scope of substrates.
Article
Pharmacology & Pharmacy
Muhammad Asim Akhtar, Zoya Hadzhieva, Kanwal Ilyas, Muhammad Saad Ali, Wolfgang Peukert, Aldo R. Boccaccini
Summary: The study demonstrated the antibacterial properties of gallium (III)-chitosan (Ga (III)-CS) complexes with six different gallium concentrations against both Gram-negative and Gram-positive bacteria, as well as their non-toxic effects on human osteosarcoma cell line (MG-63 cells) and mouse embryonic fibroblasts cell line (MEFs). This suggests the potential development of new antibiotic-free antibacterial biomaterials based on Ga (III)-CS, expanding the scope of chitosan applications in the biomedical field.
Article
Polymer Science
Qilong Li, Shaoxiang Liu, Mingfeng Xu, Xiangqiang Pan, Na Li, Jian Zhu, Xiulin Zhu
EUROPEAN POLYMER JOURNAL
(2020)
Article
Engineering, Biomedical
Zhangzhe Zhou, Yimeng Wang, Yuqing Qian, Xiangqiang Pan, Jian Zhu, Zhengbiao Zhang, Zhonglai Qian, Zhiyong Sun, Bin Pi
JOURNAL OF BIOMATERIALS SCIENCE-POLYMER EDITION
(2020)
Article
Polymer Science
Jie Zhao, Xiangqiang Pan, Jian Zhu, Xiulin Zhu
Article
Polymer Science
Qilong Li, Shaoxiang Liu, Jiajia Li, Xiangqiang Pan, Jian Zhu, Xiulin Zhu
Summary: In this study, selenium-containing maleimide polymers with different selenium contents were synthesized via radical copolymerization. The polymer structures and selenium contents were characterized using various techniques, and the refractive indices of the polymers were investigated as a function of selenium content and oxidative stimuli. A photonic crystal based on the selenium-containing polymer was prepared, and the visible color changes of the photonic crystal were studied with different concentrations and contact times of O-3.
MACROMOLECULAR RAPID COMMUNICATIONS
(2021)
Article
Polymer Science
Shaoxiang Liu, Qilong Li, Yingying Li, Jiandong Zhang, Xiangqiang Pan, Jian Zhu, Xiulin Zhu
Summary: The synthesis of selenium-containing monomer polystyrene by reversible addition-fragmentation chain transfer polymerization, as well as the structure changes during redox cycling, were studied. The properties of the polymer before and after oxidation were investigated, and a selenium-containing polymer was successfully used to fabricate inverse opal photonic crystals for use as a redox-responsive sensor, showcasing new perspectives in modulating photonic crystals.
MACROMOLECULAR RAPID COMMUNICATIONS
(2021)
Article
Polymer Science
Jiajia Li, Andrew Kerr, Qiao Song, Jie Yang, Satu Hakkinen, Xiangqiang Pan, Zhengbiao Zhang, Jian Zhu, Sebastien Perrier
Summary: A robust manganese-catalyzed cationic reversible addition-fragmentation chain transfer (RAFT) polymerization induced by visible light is presented in this study, allowing for the convenient preparation of well-defined poly(vinyl ether)s with controlled molecular weight and molecular weight distributions at room temperature. The commercially available manganese carbonyl bromide serves as the photocatalyst for this cationic RAFT polymerization. Additionally, this method is applicable in both batch and continuous flow systems, enabling a visible light induced flow cationic polymerization under mild conditions.
Article
Polymer Science
Yuanyuan Zhang, Xiangqiang Pan, Jian Zhu
Summary: Selenium-containing polystyrene microspheres were synthesized by soap-free emulsion polymerization with the diameter being adjustable by changing the ratio of monomer and crosslinker/water. The oxidized microspheres exhibited higher catalytic activity and selectivity to methyl acrylate.
Article
Chemistry, Multidisciplinary
Miao Chen, Jiajia Li, Kaiqi Ma, Guoqin Jin, Xiangqiang Pan, Zhengbiao Zhang, Jian Zhu
Summary: A method for controlling polymer MWD was presented by utilizing temporal programming and adjusting an external light source to obtain MWD curves with different widths and shapes. The strategy of latent mediator was employed, resulting in the successful preparation of bimodal, trimodal, and tetramodal distributions of polymers. The introduction of computer-controlled temporal programming for the light source also paved the way for the use of artificial intelligence in polymer synthesis.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Polymer Science
Mengmeng Zhang, Jiajia Li, Miao Chen, Xiangqiang Pan, Zhengbiao Zhang, Jian Zhu
Summary: The article introduces a new method for controlling the molecular weight distribution of polymers through photocontrol, allowing for the transformation from a latent initiator to an initiator during polymerization. This approach can produce polymers with controlled molecular weight and narrow distributions under mild conditions, demonstrating the potential for tuning MWDs in batch polymerization.
Article
Polymer Science
Qilong Li, Na Li, Xiangqiang Pan, Jian Zhu
Summary: The research investigated the effects of ultraviolet light on breaking aryl C-Se bond, alkyl C-Se bond, and alkyl C-S bond, revealing that only the C-Se bond in SePP could be broken. Under oxygen-free conditions, irradiation of SePP with UV light led to a structural change from linear to cross-linked, accompanied by a decrease in refractive index of the polymer.
EUROPEAN POLYMER JOURNAL
(2021)
Article
Chemistry, Applied
Shaoxiang Liu, Xiangqiang Pan, Jian Zhu
Summary: By photo-induced RAFT polymerization, copolymers of p-phenylseleno styrene and 4-(1,2,2-triphenylvinyl)phenyl acrylate were successfully synthesized, with selective oxidation of the selenide moiety altering the structure and properties of the copolymers. Systematic investigation of the properties of the copolymers before and after oxidation was conducted, leading to the development of a versatile and multifunctional fluorescent probe sensor.
REACTIVE & FUNCTIONAL POLYMERS
(2021)
Article
Polymer Science
Xiaofang Lin, Sisi Chen, Weihong Lu, Ming Liu, Zhengbiao Zhang, Jian Zhu, Xiangqiang Pan
Summary: The study established a method for the efficient preparation of selenium-containing hyperbranched polymers through diselenide-yne polymerization, resulting in Se-HBPs with high yields and stereoselectivity after systematic optimization of reaction conditions.
Article
Polymer Science
Xingxia Xu, Weihong Lu, Jian Zhu, Xiangqiang Pan, Xiulin Zhu
Summary: A new kind of on-demand dissolution hydrogel was successfully synthesized by modifying chitosan, demonstrating excellent biocompatibility and good degradation properties under oxidation or reduction conditions, making it promising for dressing applications.
Article
Polymer Science
Sisi Chen, Ming Liu, Jiandong Zhang, Zhengbiao Zhang, Jian Zhu, Xiangqiang Pan, Xiulin Zhu
Summary: A new dynamic C-Se bond-based reaction involving addition-fragmentation chain transfer (AFCT) without any catalyst has been developed, operating through a radical mechanism. This dynamic bond shows great potential for application in smart polymer materials.
Article
Polymer Science
Xia Lin, Jiajia Li, Jiandong Zhang, Shaoxiang Liu, Xiaofang Lin, Xiangqiang Pan, Jian Zhu, Xiulin Zhu
Summary: A living cationic polymerization of vinyl ethers was developed using electrophilic selenium reagents as initiators and pentacarbonylbromomanganese as the catalyst. This polymerization could be conducted under ambient conditions and yielded polymers with controlled molecular weights and narrow molecular weight distributions. The method also allowed for the introduction of different selenium-containing structures into the polymers.
Article
Chemistry, Organic
Geeta Devi Yadav, Pooja Chaudhary, Balaram Pani, Surendra Singh
Summary: Chiral transition metal complexes with privileged ligands are efficient catalysts for various asymmetric organic transformations. Transition metal complexes of C1-symmetric pyrrolidine-based ligands have been widely used in asymmetric organic reactions. However, a comprehensive review article on the transition metal complexes of chiral C1-symmetric pyrrolidine-based ligands derived from (L)-proline has not been published.
TETRAHEDRON LETTERS
(2024)
