Article
Chemistry, Organic
Itaru Nakamura, Kazuki Masukawa, Yasuhiro Ishida, Masahiro Terada
Summary: The reaction involves a Cu-catalyzed cascade reaction between N-alkoxyanilines and dienophiles, proceeding through a dearomative effect and Diels-Alder reaction to afford ketimines with highly functionalized bicyclic skeletons. Mechanistic investigations showed that the [1,3]-rearrangement is the rate-determining step, effectively suppressing unfavorable side reactions.
Article
Chemistry, Organic
Lingbo Han, Xin Wei, Yi Yuan, Lu Bai, Hui Wang, Xinjun Luan
Summary: In this study, a palladium-catalyzed C-H arylation/arene dearomatization reaction was performed in a redox-neutral manner. This domino reaction involved in situ-formed Pd(II) species, phenolic-group-directed C-H activation, biaryl cross-coupling, and naphthol dearomatization, leading to the rapid assembly of spiro[4,5]fluorenes with high yield and good chemoselectivity. Interestingly, the malononitrile-derived spirofluorene 6 showed mechanoresponsive luminescence and its potential application in optical memory devices.
Article
Chemistry, Organic
Shunya Hayashi, Kiyosei Takasu, Hiroshi Takikawa
Summary: This article describes a novel method for the sequential dibromination and dearomatization of 2-methoxyphenols using N-bromosuccinimide (NBS), providing rapid access to brominated ortho-quinone monoacetals (o-QMAs). This method is notable for introducing bromo group(s) into the aromatic ring and converting them into o-QMAs in a single operation, as well as using NBS as a convenient oxidant in oxidative dearomatization reactions.
Article
Chemistry, Organic
Nabakumar Bera, Bhabani Sankar Lenka, Burkhard Konig, Debayan Sarkar
Summary: Dearomative spiro-etherification of naphthols was achieved using catalytic amounts of riboflavin tetracetate (RFTA) as a photosensitizer and molecular oxygen as a terminal oxidizing agent under blue light (440 nm) irradiation in the presence of acid. The presence of acid increased the photooxidation power of RFTA and facilitated the dearomatization reaction.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Motohiro Yasui, Haruna Ohbu, Maho Ishikawa, Tatsuhito Yoshida, Norihiko Takeda, Seiya Hirao, Takumi Abe, Masafumi Ueda
Summary: Spiro[indole-3,3'-pyrrolidine]-2'-ones were synthesized via one-pot chloroformylation-dearomatizing spirocyclization of tryptamine derivatives. Additionally, the thio equivalent spiro[indole-3,3'-pyrrolidine]-2'-thiones, which were previously unreported, were synthesized. The procedures are easily implemented, have a broad scope, and are transition-metal-free and cheap. To demonstrate the utility of the synthetic methodology, the spiro[indole-3,3'-pyrrolidine]-2'-ones were converted into heterocyclic scaffolds, such as an optically active spiroindoline and spirooxindole.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Applied
Linhong Zuo, Wusheng Guo
Summary: A Pd-catalyzed decarboxylative approach for the construction of 2-allyl-2,2-diarylacetaldehydes via a dearomative umpolung strategy is presented. The reaction is applicable to various cyclic carbonates or allylic acetates with different functional groups. The reaction can be scaled up to gram-scale without loss of efficiency. Control experiments suggest that the reaction proceeds through a palladium-catalyzed dearomative decarboxylation step followed by an umpolung nucleophilic attack.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Organic
Zhenwei Lv, Yan Li, Erik V. Van der Eycken, Lingchao Cai, Liangliang Song
Summary: Here, we report a metal-free cascade cyclization reaction that constructs structurally novel polyheterocycles by utilizing a hypervalent iodine(III) reagent. Under ambient conditions, alkyne-tethered N-alkoxybenzamides undergo a 6-exo-dig cyclization/dearomatization process to generate diverse N-O fused spiro polyheterocycles in good to high yields. This method features short reaction times, broad substrate scope, easy handling, and shows promising antifungal activity against crop and forest pathogenic fungi.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Applied
Louis Peault, Servane Rochelle, Aurelien Planchat, Pierrick Nun, Erwan Le Grognec, Vincent Coeffard
Summary: This article introduces a synthesis method for epoxy dienone products starting from para-substituted phenols bearing an electron-deficient alkene. The one-pot photooxygenation/epoxidation reaction can proceed at room temperature under green light irradiation with catalytic amounts of Rose Bengal and cesium carbonate. The reaction provides a range of functionalized epoxy dienone products with diastereoisomeric ratios ranging from 4:1 to > 12:1. DFT calculations and mechanistic experiments demonstrate that the reaction proceeds through singlet oxygen-mediated photooxidation of phenols followed by an intramolecular oxygen atom transfer on the alkene side arm.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Organic
Zhenwei Lv, Yan Li, Erik V. Van der Eycken, Lingchao Cai, Liangliang Song
Summary: In this study, a metal-free cascade cyclization method was developed for the construction of structurally novel polyheterocycles. The approach involves the use of a hypervalent iodine(iii) reagent and generates diverse N-O fused spiro polyheterocycles in high yields. The synthesized compounds exhibit good antifungal activity against crop and forest pathogenic fungi, with one compound showing superior performance compared to the positive control.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Multidisciplinary
Tom D. D'Arcy, Mark R. J. Elsegood, Benjamin R. Buckley
Summary: The highly enantioselective organocatalytic tandem o-HPD-[4+2] reaction described offers a practical method for the synthesis of complex scaffolds. This approach utilizes a chiral oxaziridinium organocatalyst to afford dearomatized products in high enantioselectivity, demonstrating its potential for gram-scale applications.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Hongbo Qi, Dongmei Chi, Jing He, Leming Wang, Shufeng Chen
Summary: A facile palladium-catalyzed cascade reaction of intramolecular Heck cyclization and alkylpalladium activated dearomatization of aryl alkynetethered indole is described. This single-step transformation efficiently provides two nonadjacent quaternary carbon centers, two nitrogen-containing heterocycles, and three C(sp2)-C(sp3) bonds. The resulting products can also undergo ring migration-expansion reaction under Bronsted-acid conditions, leading to benzo[c]carbazole skeletons.
Article
Chemistry, Organic
Hui Yang, Wen-Lei Xu, Xin-Yi Zeng, Jie Chen, Le Yu, Ling Zhou
Summary: The asymmetric construction of chiral spiroenones has been achieved for the first time by utilizing hydrogen bonds to control both spiro-central and axial chirality in one operation. This study provides an efficient strategy for the enantioselective construction of spirocyclic backbones.
Article
Chemistry, Organic
Jiang Zhu, Jiaji Li, Lianjie Zhang, Shitao Sun, Lu Yang, Jiayue Fu, Hanyang Sun, Maosheng Cheng, Bin Lin, Yongxiang Liu
Summary: Spiro[indoline-3,3′-pyrrolidine] and spiro[indoline-3,3′-piperidine] derivatives were synthesized in a substitution-controlled manner using cationic gold(I) catalyst and Hantzsch ester (HEH). The optimal reaction conditions were determined by screening, and the functional group tolerances of these pathways were examined using synthetic substrates. Density functional theory calculations elucidated the endo and exo selectivities of these cyclizations, and a plausible mechanism for these transformations was proposed.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Dong Xia, Liu-Yu Shen, Yicheng Zhang, Wen-Chao Yang
Summary: In this work, we report on a new N-centered radical initiated spirocyclization of biaryl ynones under metal- and additive-free conditions. This approach features good functional group tolerance and provides a facile and green way for the construction of NO2-containing spiro[5.5]trienones.
NEW JOURNAL OF CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Hong Liu, Kai Li, Shengli Huang, Hailong Yan
Summary: This study reports the first isolation and comprehensive characterization of vinylidene orlho-quinone methides (VQMs), demonstrating their significant role in asymmetric catalysis and potential as starting materials.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Multidisciplinary Sciences
Ian A. MacKenzie, Leifeng Wang, Nicholas P. R. Onuska, Olivia F. Williams, Khadiza Begam, Andrew M. Moran, Barry D. Dunietz, David A. Nicewicz
Article
Multidisciplinary Sciences
Jing Yang, Wei Yin, Richard Van, Keyi Yin, Peng Wang, Chao Zheng, Biyue Zhu, Kathleen Ran, Can Zhang, Mohanraja Kumar, Yihan Shao, Chongzhao Ran
NATURE COMMUNICATIONS
(2020)
Article
Chemistry, Physical
Lu Wang, Ting Wang, Gui-Juan Cheng, Xiaobao Li, Jun-Jie Wei, Bin Guo, Caijuan Zheng, Guangying Chen, Chongzhao Ran, Chao Zheng
Review
Biochemistry & Molecular Biology
Haonan Li, Fanxing Xu, Gang Gao, Xiang Gao, Bo Wu, Chao Zheng, Peng Wang, Zhanlin Li, Huiming Hua, Dahong Li
Article
Multidisciplinary Sciences
Fengjin Wu, Leifeng Wang, Ying Ji, Ge Zou, Hong Shen, David A. Nicewicz, Jiean Chen, Yong Huang
Review
Chemistry, Medicinal
Yuxi Fang, Haonan Li, Bao Ji, Keguang Cheng, Bo Wu, Zhanlin Li, Chao Zheng, Huiming Hua, Dahong Li
Summary: Renieramycins, a member of tetrahydroisoquinoline family of marine natural products, show strong antitumor activities with potential for further drug development and innovation. Researches mainly focus on their pharmacological activities and structural modification for enhanced anti-proliferative effects. However, challenges in extraction and separation hinder their development.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2021)
Review
Chemistry, Analytical
Haonan Li, Yuxi Fang, Junjie Yan, Xiangyu Ren, Chao Zheng, Bo Wu, Siyuan Wang, Zhanlin Li, Huiming Hua, Peng Wang, Dahong Li
Summary: Hydrogen sulfide (H2S) is considered as another gasotransmitter involved in important physiological and pathological processes. To real-time detect H2S in biological systems, numerous small-molecule fluorescent probes have been developed, with improvements in selectivity, response capability, and optical performance.
TRAC-TRENDS IN ANALYTICAL CHEMISTRY
(2021)
Review
Pharmacology & Pharmacy
Xu Hu, Yan Xiao, Jianan Sun, Bao Ji, Shanshan Luo, Bo Wu, Chao Zheng, Peng Wang, Fanxing Xu, Keguang Cheng, Huiming Hua, Dahong Li
Summary: Pancreatic cancer is a deadly disease with poor prognosis and resistance to treatments. The gasotransmitter hydrogen sulfide (H2S) has shown potential in modulating cancer development, with exogenous H2S donors being considered as promising compounds for pancreatic cancer therapy.
ACTA PHARMACEUTICA SINICA B
(2021)
Article
Chemistry, Analytical
Chao Zheng, Yue Yu, Shi Kuang, Biyue Zhu, Heng Zhou, Shao-Qing Zhang, Jing Yang, Liang Shi, Chongzhao Ran
Summary: The study demonstrates a new approach to alter the switching behavior of DASA through DASA-peptide/protein interactions. Experimental results show that the designed DASA compound SHA-2 can stabilize the linear conformation of the A beta 40 species and alter its tertiary structure, thereby reducing the rate of molecular switching.
ANALYTICAL CHEMISTRY
(2021)
Review
Chemistry, Analytical
Jian Qiao, Mingying Wang, Menghan Cui, Yuxi Fang, Haonan Li, Chao Zheng, Zhanlin Li, Yongnan Xu, Huiming Hua, Dahong Li
Summary: Nitroreductase catalyzes the conversion of nitro aromatic compounds to aromatic amines. Its upregulation in hypoxic tumor cells is directly related to the degree of hypoxia, making effective detection of nitroreductase important for cellular hypoxia studies, tumor diagnosis, and treatment. The latest advances in small-molecule fluorescent probes for nitroreductase detection and the development trends in this field were summarized in this review.
JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS
(2021)
Article
Radiology, Nuclear Medicine & Medical Imaging
Chao Zheng, Daniel Holden, Ming-Qiang Zheng, Richard Pracitto, Kyle C. Wilcox, Marcel Lindemann, Zachary Felchner, Li Zhang, Jie Tong, Krista Fowles, Sjoerd J. Finnema, Nabeel Nabulsi, Richard E. Carson, Yiyun Huang, Zhengxin Cai
Summary: This study developed a novel SV2A PET tracer [F-18]SDM-16 with high binding affinity and metabolic stability, which showed excellent specific and reversible binding in nonhuman primate brains, demonstrating potential applications beyond the brain for the visualization and quantification of SV2A.
EUROPEAN JOURNAL OF NUCLEAR MEDICINE AND MOLECULAR IMAGING
(2022)
Article
Chemistry, Multidisciplinary
Richard Pracitto, Kyle C. Wilcox, Marcel Lindemann, Jie Tong, Chao Zheng, Songye Li, Sjoerd J. Finnema, Yiyun Huang, Zhengxin Cai
Summary: A series of synaptic vesicle protein 2A (SV2A) ligands were synthesized to investigate the structure-activity relationship and hydrogen bonding pharmacophore hypothesis, leading to the discovery of highly potent analogs including a 3-iodo pyridinyl ligand suitable for PET or SPECT imaging agent exploration.
Review
Biochemistry & Molecular Biology
Haijun Yang, Fantian Zeng, Yunchun Luo, Chao Zheng, Chongzhao Ran, Jian Yang
Summary: Alzheimer's disease (AD) is a common neurodegenerative disorder characterized by amyloid-beta plaques and neurofibrillary tangles. Curcumin derivatives have shown potential in AD diagnosis and therapy due to their neuroprotective effects.
Article
Chemistry, Multidisciplinary
Manhong Li, Siqi Liu, Haoshi Bao, Qini Li, Yi-Hui Deng, Tian-Yu Sun, Leifeng Wang
Summary: Organoboron compounds are valuable in medicinal, biological, and industrial fields. This study achieved direct borylation of haloarenes without the use of metal catalysts by irradiating with visible light. Mechanistic experiments and computational investigations revealed the formation of an excited donor-acceptor complex with a high reduction potential, enabling single-electron-transfer reactions with aryl halides.
