Article
Chemistry, Organic
Kai Zhou, Shendan Xia, Zhiwei Chen
Summary: An electrochemical-oxidation-induced intramolecular annulation was developed for the synthesis of quinoxalines under undivided electrolytic conditions. N-Aryl enamines and TMSN3 smoothly participated in the transformation, achieving the construction of two C-N bonds through tandem azidation and cyclic amination reactions. The reaction is easily handled and avoids the use of transition metal catalysts and chemical oxidants, making it compatible with the sustainable development of green chemistry.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Organic
Zhishuang Wang, Youwen Fei, Chongrong Tang, Lei Cui, Jie Shen, Kun Yin, Shanya Lu, Jian Li
Summary: The multicomponent protocol reported in this study allows for the assembly of several polycyclic dihydropyran-fused tetrahydroquinoline structures with excellent diastereoselectivity, using simple feedstocks to achieve a series of diverse structures that are difficult to attain by traditional sequences.
Article
Chemistry, Organic
Hao Yuan, Yu-Zheng Wu, Yu-Han Fang, Chun-Hua Chen, Cui Liang, Dong-Liang Mo
Summary: A variety of spirooxindole-1,2-oxazinan-5-one derivatives were synthesized using 2,2,2-trifluoroethanol-promoted [3 + 3] cycloaddition. Mechanistic studies revealed possible reaction pathways and highlighted the advantages of this method.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Pharmacology & Pharmacy
Huajie Li, Zhenjie Yu, Haoyi Sun, Bo Liu, Xin Wang, Zhe Shao, Meiling Wang, Weilin Xie, Xingang Yao, Qingqiang Yao, Ying Zhi
Summary: A novel reaction between N-(o-chloromethyl)aryl amides and 3-chlorooxindoles has been reported for the synthesis of a series of 2,3'-spirobi(indolin)- 2'-ones in high yields. Compound 3a was found to change mitochondrial morphology and induce mitophagy pathway, potentially triggering mitophagy in cancer cells.
FRONTIERS IN PHARMACOLOGY
(2022)
Review
Chemistry, Medicinal
Antonio Rosales Martinez, Ignacio Rodriguez-Garcia, Josefa L. Lopez-Martinez
Summary: The divergent total synthesis strategy is successfully applied to prepare families of natural products using a common late-stage pluripotent intermediate, offering opportunities for the efficient preparation of structurally related compounds. This approach is illustrated with the synthesis of the marine natural product aureol and its use as a common intermediate in the synthesis of other marine natural and non-natural tetracyclic meroterpenoids.
Article
Chemistry, Organic
Y. Bharath Chaithanya Kumar, Polasani Samatha, Prathama S. Mainkar, Raju Adepu
Summary: Rhodium catalyzed alkyne-tethered intramolecular annulation has been successfully demonstrated for the synthesis of tetracyclic carbazole skeletons, resulting in a series of five to eight-membered pyrido[3,2,1-jk]carbazoles. This atom economical annulation proceeds under mild reaction conditions and offers a broad substrate scope.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Hai-Long Xin, Xiaofeng Rao, Haruro Ishitani, Shu Kobayashi
Summary: A sequential continuous-flow system has been developed for the efficient synthesis of 3-aryl benzofuranones. The initial cyclocondensation and subsequent Friedel-Crafts alkylation were catalyzed by the same heterogeneous catalyst, leading to the preparation of a commercial antioxidant with high yield. Reactions with various aromatic compounds proceeded well under flow conditions, providing high yields of 3-aryl benzofuranone derivatives with good functional group compatibility.
CHEMISTRY-AN ASIAN JOURNAL
(2021)
Article
Chemistry, Multidisciplinary
Yang Gao, Simin Yang, Minwei She, Jianhong Nie, Yanping Huo, Qian Chen, Xianwei Li, Xiao-Qiang Hu
Summary: We report a practical route for the synthesis of valuable 3-aryl anthranils from readily available anthranils and simple arenes using electrophilic aromatic substitution (EAS) strategy. The method shows good compatibility with a wide range of arenes and delivers various structurally diversified 3-aryl anthranils in good yields and high regioselectivity. The synthesized 3-aryl anthranils are proven to be a highly robust platform for accessing biologically active compounds, drug derivatives, and organic optoelectronic materials.
Article
Multidisciplinary Sciences
Xiangfeng Lin, Xianghui Liu, Kai Wang, Qian Li, Yan Liu, Can Li
Summary: The study introduces a novel catalytic system for an asymmetric hetero-Diels-Alder reaction, leading to the synthesis of diverse tetracyclic isochroman frameworks with excellent stereoinduction. The key reaction involves a stepwise pathway, with steric hindrance playing a role in enantioselectivity.
NATURE COMMUNICATIONS
(2021)
Article
Chemistry, Applied
Dirgha Raj Joshi, Ikyon Kim
Summary: In this study, a modular approach was used to synthesize a wide range of 1-cyano-3-(hetero)arylindolizines through aldol-cyclopropanation-oxidative cycloisomerization. DDQ was utilized for the first time to selectively synthesize the pyrrole units from cyclopropyl pyridines. The regioselective oxidation of the benzylic position by DDQ enabled the access to one regioisomer out of two possible ones. Additionally, homo-dimerization at the C2, C5, or C7 sites of indolizines in the presence of DDQ was discovered for the first time.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Organic
Shao-Yong Chen, Yao-Fu Zeng, Wen-Xuan Zou, Dan-Ting Shen, Yi-Chuan Zheng, Jia-Lin Song, Shang-Shi Zhang
Summary: Two categories of tetrasubstituted phenols were synthesized through a cycloaddition reaction, where copper carbenoid was proposed as the active intermediate for the formation of 2,3,4,5-tetrasubstituted phenols and 2,3,5,6-tetrasubstituted phenols were generated via a metal-free [3 + 3] annulation reaction. Additional synthetic applications were also demonstrated.
Article
Chemistry, Organic
Shao-Long Qi, Yue Li, Jiang-Fei Li, Tao Zhang, Yu-Xin Luan, Mengchun Ye
Summary: The study successfully demonstrated the dual C-H annulation of N-aromatic imidazole using a base-metal Ni catalyst, yielding a range of desired polycyclic aza-quinolines in 48-95% yields. The use of bifunctional phosphine oxide ligand was crucial for the success of the reaction.
Article
Chemistry, Organic
Zhi-Yi Zhao, Xing-Guo Zhang, Hai-Yong Tu
Summary: A palladium-catalyzed cyclization reaction of phenols with trifluoromethyl-containing ortho-bromo-beta-chlorostyrenes has been developed, leading to the synthesis of 6-trifluoromethyldibenzo[b,d]oxepines through a tandem O-alkenylation and subsequent C-H arylation.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Meng-Yang Chang, Chun-Yi Lin, Shin-Mei Chen, Yu-Ting Hsiao
Summary: The one-pot tandem annulation mediated by Bi(OTf)3 provides a highly effective method for synthesizing polyoxygenated homotriptycenes under easy-operational conditions. The protocol involves intermolecular and intramolecular Friedel-Crafts type procedures, leading to moderate to good yields in a short reaction time.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Organic
Linghua Zhang, Jie Zhao, Yuqin Jiang, Xinying Zhang, Xuesen Fan
Summary: This paper presents a novel and efficient synthesis method for tetracyclic indenopyrazolopyrazolone derivatives through cascade reactions, demonstrating advantages of accessibility and potential pharmaceutical applications.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Organic
Zenghui Ye, Hong Zhang, Na Chen, Yanqi Wu, Fengzhi Zhang
Article
Multidisciplinary Sciences
Zenghui Ye, Yanqi Wu, Na Chen, Hong Zhang, Kai Zhu, Mingruo Ding, Min Liu, Yong Li, Fengzhi Zhang
NATURE COMMUNICATIONS
(2020)
Article
Chemistry, Organic
Mingruo Ding, Wenkai Hua, Min Liu, Fengzhi Zhang
Article
Chemistry, Multidisciplinary
Hong Zhang, Zenghui Ye, Na Chen, Zhenkun Chen, Fengzhi Zhang
Summary: An electrochemical method using easily available hydrazones has been developed for the synthesis of 1H-indazoles. This metal- and oxidant-free protocol is compatible with various functional groups and can be carried out on a gram-scale under neutral and mild conditions. The method has been successfully applied to the efficient synthesis of anti-tumor compounds. Mechanism studies suggest the involvement of a radical pathway, with an important role played by HFIP.
Article
Chemistry, Organic
Zenghui Ye, Rongjin Zhu, Feng Wang, Haobin Jiang, Fengzhi Zhang
Summary: Atom- and step-economic oxo-azidation and oxo-hydroxyphthalimidation of styrenes were developed under mild electrolytic conditions, leading to efficient synthesis of valuable alpha-azido or hydroxyphthalimide aromatic ketones from readily available starting materials. Mechanism studies revealed two different pathways involved in these transformations.
Article
Chemistry, Organic
Zongqiang Song, Kai Zhu, Hongqiang Jiang, Hengfa Gong, Zenghui Ye, Fengzhi Zhang
Summary: A simple and novel method for the synthesis of 1,3-dioxepine-fused (tricyclic) bispyrazoles is described. The protocol involves O-alkylation and intramolecular oxidative biheteroaryl coupling under mild conditions. The synthesized compounds have potential applications in medicinal or material chemistry.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Linwei Zeng, Fengzhi Zhang, Sunliang Cui
Summary: A modular and practical click chemistry is developed for the atroposelective synthesis of 1-triazolyl-2-naphthylamines. This method involves a [3 + 2] cycloaddition reaction under Rh-catalysis to assemble various aromatic or aliphatic azides with 1-alkynyl-2-naphthylamines, resulting in valuable 1-triazolyl-2-naphthylamine scaffolds. This asymmetric click technology offers easily accessible starting materials, mild reaction conditions, facile scalability, and good enantioselectivity. The thermostability of the products highlights their great potential for applications, while the synthetic transformations further enhance the molecular diversity of atropisomers.
Article
Chemistry, Medicinal
Xiang Li, Lina Yin, Jing Liao, Jun Yang, Binhao Cai, Yiming Yu, Sijia Su, Zhiteng Du, Xiaobo Li, Ying Zhou, Pan Chen, Won-Jea Cho, Nipon Chattipakorn, Aleksandr V. Samorodov, Valentin N. Pavlov, Fengzhi Zhang, Guang Liang, Qidong Tang
Summary: A series of novel O-benzylcinnamic acid derivatives were designed and synthesized, and compound L26 showed the best anti-inflammatory activity, being 7-fold more active than CIN. Further experiments revealed that L26 targeted MD-2 protein and competed with LPS to bind to MD-2, resulting in inflammation inhibition. In vivo experiments demonstrated that high doses of L26 were safe and it exhibited optimal pharmacodynamic and pharmacokinetic characteristics, suggesting its potential as a treatment agent for ALI.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2023)
Article
Chemistry, Organic
Min Liu, Haobin Jiang, Jiyuan Tang, Zenghui Ye, Fengzhi Zhang, Yanqi Wu
Summary: Here, a base-mediated, highly meta-selective O-arylation process of phenols and cyclic diaryliodonium salts without the use of transition metals is reported. This novel and practical method has been demonstrated to be useful for the synthesis of iodine-containing meta-functionalized biaryl ethers with a broad functional group tolerance and environmental friendliness. Diverse transformations of the products have been conducted to obtain various valuable functionalized biaryls. Preliminary mechanistic studies provide support for the proposed aryne generation mechanism.
Article
Chemistry, Organic
Zhenkun Chen, Fengzhi Zhang
Summary: The Catellani reaction is a palladium-catalyzed hydrocarbon-activated multicomponent tandem reaction that involves an aryl halide, an electrophilic coupling reagent, and a terminating reagent. Norbornenes serve as co-catalysts and play critical roles in this reaction. After more than two decades of development, the Catellani reaction has become a unique method for the synthesis of poly-functionalized aromatics from easily accessible starting materials, with advantages of cross-coupling and adjacent metallization, as well as excellent reactivity and wide applicability. This manuscript reviews the important advances in Catellani reactions over the last four years, providing valuable insights for researchers in this prosperous research area.
Article
Chemistry, Organic
Huaipu Yan, Jing-Ran Shan, Fengzhi Zhang, Yuqing Chen, Xinyi Zhang, Qian Liao, Erjun Hao, Lei Shi
Summary: A radical strategy using metal-hydride hydrogen atom transfer (MHAT) via photoredox cobalt and titanium dual catalysis is reported for alkene functionalization. The method achieves excellent regio- and diastereoselectivity.
Article
Chemistry, Multidisciplinary
Min Liu, Yong Qian, Yanqi Wu, Fengzhi Zhang
Summary: A multicomponent, environmentally friendly protocol has been developed to generate di-aryl dithiocarbamates from readily available thianthrenium salts. The reaction can be smoothly conducted using both aromatic and alkyl amines without the need for photocatalysts, transition-metal catalysts, or ligands. A novel photoactivated electron donor-acceptor complex is proposed as the key intermediate. This protocol offers a new approach towards di-aryl dithiocarbamates and shows promise for potential applications in pharmaceutical chemistry and sulfur chemistry.
Article
Chemistry, Multidisciplinary
Zhide Zhang, Yangling Deng, Ming Hou, Xiaojing Lai, Meng Guan, Fengzhi Zhang, Rui Qi, Guanyinsheng Qiu
Summary: This paper describes iron/photoredox dual-catalyzed acyl nitrene formation and its application in constructing various C-O bonds towards phthalides. The reaction starts from N-methoxyl-2-alkylbenzamides. Mechanistic studies suggest that the reaction involves iron nitrene-based hydrogen atom abstraction (HAA), radical-polar crossover, and O-nucleophilic S(N)1. Radical rebound, commonly observed in previous publications, is not observed in this reaction. This reaction represents the first example of acyl nitrene-based synthesis of phthalides and has potential applications in the synthesis of marketed medicines.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Linwei Zeng, Shuheng Xu, Sunliang Cui, Fengzhi Zhang
Summary: The multicomponent reaction described for the synthesis of beta-aminoxy amides offers various advantages such as readily available starting materials, high atom economy, mild reaction conditions, and easy scalability. Control reactions and a crossover experiment have provided insights into the possible mechanism of the reaction.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Review
Chemistry, Organic
Na Chen, Zenghui Ye, Fengzhi Zhang
Summary: Carboxylic acids are crucial components in medicinal molecules, natural products, and agrochemicals, as well as basic building blocks for organic synthesis. Organic electrochemistry, as an environmentally friendly and sustainable synthetic method, offers a promising alternative to traditional high-temperature, costly, and oxidant-heavy carboxylic acid group transformations.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)