Review
Chemistry, Organic
Giorgio Molteni, Alessandra Silvani
Summary: This paper discusses the developments in spirooxindole synthesis via a 1,3-dipolar cycloaddition that occurred in the 2011-2020 decade. Literature data on this subject are systematically reviewed according to the types of 1,3-dipole and oxindole dipolarophile.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Souvik Guha, Satyanarayana Gadde, Naresh Kumar, David StClair Black, Subhabrata Sen
Summary: A series of telescoping methodologies were reported for the one-pot synthesis of biologically relevant β-carboline derivatives 6 and spiro[pyrrolidinone-3,3']indole 7. Careful optimization of the reaction sequence and conditions allowed for the exclusive access to compounds 6 and 7. Air oxidation of gamma-carbolinones 6 yielded aromatic gamma-carbolines 8.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Alexander Aksenov, Dmitrii A. Aksenov, Nicolai A. Aksenov, Anton A. Skomorokhov, Elena Aleksandrova, Michael Rubin
Summary: This study utilized a highly efficient one-pot procedure to prepare diastereomerically selective 4'H-spiro[indole-3,5'-isoxazoles] by combining conjugate addition of Grignard reagents to (2-nitroalkenyl)indoles with subsequent Bronsted acid-assisted spirocyclization. The use of alkyl Grignard reagents provided easy access to 4'-alkylsubstituted derivatives that are difficult to obtain by other means.
Article
Chemistry, Organic
Shuai-Jiang Liu, Qing Mao, Ya-Jun Zhong, Jing Xue, Ben-Hong Chen, Qian Zhao, Wei Huang
Summary: A highly diastereoselective 1,3-dipolar cycloaddition reaction was developed for the synthesis of a wide range of isoxazole- and trifluoromethyl-containing spiro[pyrrolidin-oxindoles] with high yields and excellent diastereoselectivities. Further transformations of the final products and the gram-scale capacity of this method were also evaluated.
TETRAHEDRON LETTERS
(2021)
Article
Chemistry, Organic
Abhijit Manna, Harshit Joshi, Vinod K. Singh
Summary: A novel organocatalytic cascade approach has been developed for the synthesis of spiro-cyclopropyl oxindole derivatives. This methodology demonstrates remarkable stereocontrol, wide substrate scope, and scalability, and represents the first example of vinylogous Michael initiated ring closure reaction for the synthesis of chiral 3,3'-cyclopropyl oxindole.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Peiran Ruan, Cefei Zhang, Jin Wu, Fengnan Xiao, Yongyan Zhang, Qingfa Tan, Zhishan Su, Xiaoming Feng, Xiaohua Liu
Summary: By utilizing newly designed alpha-imino amide surrogates and azlactones as reactants, catalyzed by a chiral bifunctional guanidine, the construction of chiral 3,4-diaminopyrrolidine-2,5-diones and their derivatives was achieved through formal [3+2]-cyclization. The DFT calculations confirmed the role of guanidine as a multiple hydrogen bond donor.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Medicinal
Shuai-Jiang Liu, Qian Zhao, Cheng Peng, Qing Mao, Fengbo Wu, Feng-Hua Zhang, Quan-Sheng Feng, Gu He, Bo Han
Summary: A series of highly active compounds containing CF3 group were synthesized as novel inhibitors of GPX4 and MDM2, with compound 3d exhibiting excellent activity in suppressing MDM2-mediated degradation and GPX4 levels in MCF-7 breast cancer cells. Moreover, 3d also showed inhibitory effects on MDM2 and GPX4 in MCF-7 xenograft model, inducing ferroptotic and apoptotic cell death in vivo experiments.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Yu Zhang, Yanchuan Li, Shao-Fei Ni, Jin-Peng Li, Dingding Xia, Xinyu Han, Jingchuan Lin, Jinxin Wang, Shoubhik Das, Wei-Dong Zhang
Summary: Visible-light-induced [3+2] cycloadditions of donor/donor diazo precursors with alkenes to afford pyrazoles and (spiro)pyrazolines have been reported. Mechanistic and DFT studies suggested the non-covalent interactions promote the reaction.
Article
Chemistry, Multidisciplinary
Yu Zhang, Yanchuan Li, Shao-Fei Ni, Jin-Peng Li, Dingding Xia, Xinyu Han, Jingchuan Lin, Jinxin Wang, Shoubhik Das, Wei-Dong Zhang
Summary: Visible-light-induced [3+2] cycloadditions of donor/donor diazo precursors with alkenes to afford pyrazoles and (spiro)pyrazolines have been reported. Mechanistic and DFT studies suggested the formation of non-covalent interactions promote the reaction.
Article
Chemistry, Organic
Vladislav Yu Korotaev, Nikolay S. Zimnitskiy, Andrey D. Denikaev, Alexey Yu Barkov, Igor B. Kutyashev, Vyacheslav Ya Sosnovskikh
Summary: The three-component reaction involving (E)-1,5-diarylpent-4-ene-1,3-diones, isatins, and (thia)proline in i-PrOH at room temperature selectively produces spiro[(thia)pyrrolizidine-3,3'-oxindoles] with a 1,3-dicarbonyl moiety. Subsequent treatment of these tetracyclic products with arylhydrazine hydrochlorides in the EtOH-AcOH system under reflux conditions leads to high yields of 5-substituted 1,3-diaryl-1H-pyrazoles.
CHEMISTRY OF HETEROCYCLIC COMPOUNDS
(2021)
Article
Chemistry, Organic
Xiao-Long He, Cheng Wang, You-Wu Wen, Yi-Bing Zhao, Huan Yang, Shan Qian, Lingling Yang, Zhouyu Wang
Summary: A highly stereoselective dearomative [3 + 2] cycloaddition between cyclic pyridinium ylides and nitroolefins has been developed, using novel cyclic pyridinium salts as ylide precursors. This protocol offers advantages such as broad substrate scope, mild conditions, high yield, and stereoselectivity, providing a concise and efficient method for the construction of spiro-indolizidine scaffolds.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Multidisciplinary
Tishyasoumya Bera, Bandana Singh, Manoranjan Jana, Jaideep Saha
Summary: Herein, a transition metal-free approach for accessing 3,3’-disubstituted peroxyoxindole is disclosed, utilizing a transient azaoxyallyl cation. This strategy is also applicable to the synthesis of structurally diverse alpha-peroxycarboxylic acid surrogates, showing good functional group tolerance and the potential to generate a library of peroxy-containing compounds.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Multidisciplinary
Eva M. Gulotty, Kevin X. Rodriguez, Erin E. Parker, Brandon L. Ashfeld
Summary: An efficient strategy for constructing spirooxindole benzofurans through a (4+1)-cycloaddition was presented, involving an isatin-derived oxyphosphonium enolate. Mechanistic investigations showed a correlation between phosphonium enolate structure and product distribution, which was heavily influenced by solvent and reaction temperature.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Organic
Jianming Zhang, Zheng Liang, Simiao Zhang, Lei Chen, Xiaoxue Wang, Yuchan Wang, Jie Feng, Tao Lu, Ding Du, Jian Gao
Summary: An N-heterocyclic carbene-catalyzed asymmetric [3 + 2] annulation of enals with propargylic ketimines has been developed for the facile and enantioselective construction of gamma, gamma-disubstituted pyrrolidin-2-ones. This method features mild reaction conditions, wide functional group tolerance, easy scalability, and high level of enantioselectivity, enriching the chemistry of NHC-bound homoenolates involved in the synthesis of gamma-lactams bearing gamma-quaternary stereogenic centers from acyclic ketimines.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Zhi-Hao You, Yan-Kai Liu
Summary: A novel [4+2] cyclization reaction was developed for the asymmetric synthesis of polycyclic compounds containing chromane and spirooxindole moieties. The reaction proceeded via intramolecular E1cB elimination and produced products with good yields (up to 84%) and excellent enantioselectivities (most 98 to >99% ee) using a chiral bifunctional thiourea-tertiary amine catalyst (1-5 mol%).
Article
Chemistry, Multidisciplinary
Kaiye Wang, Yanan Xiang, Wei Pan, Hongyu Wang, Na Li, Bo Tang
Summary: In this study, an endoplasmic reticulum-targeted organic photothermal agent was developed to enhance the efficacy of photothermal therapy for tumors. The photothermal agent exhibited excellent targeting ability and biocompatibility, and effectively eradicated tumor cells using near-infrared laser.
CHINESE CHEMICAL LETTERS
(2022)
Article
Chemistry, Physical
Jiaping Wu, Yanfei Liu, Baiyang Qian, Haitao Yang, Lili Lu, Jitan Zhang, Yongjia Shang
Summary: Catalytic ring expansion is a powerful method for the synthesis of complex molecules. In this study, a catalytic ring-expanding reaction of indoles was developed using cationic palladium(II) complexes. This reaction provides a concise access to a seven-membered azaheterocycle. The reaction is enabled by a bifunctional quinolinyl group and is compatible with a wide range of functional groups. It simplifies the synthesis of challenging dibenzoazepine analogues.
Article
Chemistry, Applied
Wenbo Hu, Liqin Yan, Youpeng Zuo, Shuwen Kong, Yue Pu, Qiang Tang, Xinyu Wang, Xinwei He, Yongjia Shang
Summary: A cascade C-H activation, annulation, and etherification reaction has been developed for the flexible synthesis of N-alkoxylated 3-arylisoindolin-1-ones. This method generates three new bonds (C-C, C-N, and C-O) to afford a series of tetrasubstituted isoindolin-1-ones with yields ranging from 49% to 82%. The utility of this method has been demonstrated through gram-scale synthesis and synthetic transformations to access structurally diverse isoindolinones.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Applied
Qiang Tang, Keke Xu, Xinwei He, Yongjia Shang
Summary: A metal-free cascade annulation strategy has been developed for the synthesis of polysubstituted imidazoles and 4-alkenylquinazolines. The reaction proceeds through sequential conjugate addition, annulation/aromatization, and nucleophilic addition/elimination/aromatization steps. The method shows broad substrate scope and high yields, as demonstrated by gram-scale experiments and synthetic transformations.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Applied
Haixia Zhao, Yuchen Jiang, Tongqing Weng, Yongjia Shang, Jian Wang
Summary: A three component construction of conjugated 1,3-dienes bearing oxindoles or isoquinolinediones from alkenylated aryl iodides, allenes and diazo compounds via a palladium catalyzed sequential alkene/allene/carbenoid insertion reaction was developed. Three C-C bonds were formed in high order, offering access to multi-substituted dienes in high yields and up to > 20:1 E/Z selectivities. The reaction features excellent functional groups tolerance under mild conditions.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Biochemistry & Molecular Biology
Xueying Wang, Jiling Feng, Rong Wu, Jiaqi Tan, Qing Huang, Yeelin Phang, Li Zhang, Wenwei Fu, Hongxi Xu, Changwu Zheng
Summary: This research aims to thoroughly evaluate the potential of Garcinol and its analogues in terms of synthesis, structural diversity, biosynthesis, and prevention of carcinoma cell proliferation. Garcinopicrobenzophenone and eugeniaphenone were synthesized and their structures were clarified. The synthesis also proposed a possible biogenetic synthesis pathway. The cytotoxicity and mechanism of action of the polyisoprenylated benzophenones were studied, showing potential as chemotherapeutic agents in pancreatic cancer cells.
BIOORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Hao Wu, Shuguang Chen, Dengmengfei Xiao, Feng Li, Kaiyuan Zhou, Xiaocui Yin, Chunni Liu, Xinwei He, Yongjia Shang
Summary: The deconstructive alkynylation of an unstrained ketone catalyzed by an organic photocatalyst under blue light irradiation is reported for the first time. The practicality of this novel alkynylation method is demonstrated through a broad substrate scope with up to 63 examples, excellent functional group tolerance, and gram scale reaction. The dihydroquinazolinone derivative of trifluoroacetophenone has been proven to have potential as a novel trifluoromethylation reagent after successful trifluoromethylation reactions with various alkynyl bromides.
Article
Chemistry, Organic
Guangzheng Tian, Mingtong Ji, Fan Wu, Guan Wang, Changwu Zheng, Xiaoyu Wu
Summary: A diastereo- and enantioselective propargylic substitution reaction was performed between propargylic carbonates and 2,2,2-trifluoroethyl-substituted nitroisoxazoles catalyzed by a Cu-pybox complex. This method enables the preparation of propargylation products with two contiguous stereogenic centers, one of which is a chiral trifluoromethyl-bearing carbon. The desired products were produced in high yields with good to excellent diastereo- and enantioselectivities in most cases.
Article
Chemistry, Analytical
Gan Chen, Hong Zhang, Jiaming Jiang, Simin Chen, Hongmei Zhang, Gongmin Zhang, Changwu Zheng, Hongxi Xu
Summary: This study aimed to differentiate mountain-cultivated ginseng by age using LC-MS analysis and machine learning models. The study successfully predicted the age group of ginseng samples based on identified biomarkers.
JOURNAL OF SEPARATION SCIENCE
(2023)
Article
Chemistry, Organic
Fan Wu, Zhiming Li, Chao Fu, Guan Wang, Changwu Zheng, Xiaoyu Wu
Summary: The asymmetric α-allylation of α-aryl-substituted 2-acetylimidazoles using Ni/Pd catalysts was successfully developed. The reaction involves the activation of the enolate of an acetyl imidazole by a nickel-bisoxazoline complex, followed by a reaction with a π-allylpalladium electrophile generated from an allyl alcohol derivative using a palladium-based catalyst. The broad substrate scope and the gram-scale reaction demonstrated the utility of this method.
Article
Chemistry, Organic
Yanan Liu, Pui Ying Choy, Demao Wang, Mengdi Wu, Qiang Tang, Xinwei He, Yongjia Shang, Fuk Yee Kwong
Summary: A 1,8-diazabicyclo[5.4.0]-undec-7-ene-promoted cascade double-annulation of ortho-alkynyl quinone methide is developed for constructing of 2-aryl-4-hydroxybenzo-[c]-chromen-6-ones. This method offers operational simplicity and good functional group compatibility.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Shuguang Chen, Jiahong Tan, Hao Wu, Quansheng Zhao, Yongjia Shang
Summary: A novel tandem method for synthesizing 2-azaaryl indoline through the reaction of 2-azaaryl methyl amine and 2-fluoro benzyl bromides promoted by LiN(SiMe3)2 was developed. Mechanistic investigation revealed that this cyclization reaction is initiated by selective benzyl C-SN2 substitution followed by an intramolecular SNAr reaction.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Organic
Xinwei He, Demao Wang, Yanan Liu, Mengdi Wu, Yangzilin Kong, Qiang Tang, Yiping Wang, Chenli Fan, Yongjia Shang
Summary: A facile method for the synthesis of furan fused heterocyclic compounds has been developed using a regioselective cascade reaction. This reaction involves multiple steps and allows the formation of highly sterically congested products. The strategy described is easily scalable and allows for further synthetic transformations.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Hongyu Wang, Ming Joo Koh
Summary: Generating value-added compounds from abundant feedstock chemicals through simple methods is a longstanding objective in organic synthesis. Regioselective three-component 1,2-dicarbofunctionalization of unactivated alkenes has emerged as a powerful strategy, but inherent challenges have hindered its development. The directing group-free approach represents a promising method for implementing 1,2-dicarbofunctionalization.
CELL REPORTS PHYSICAL SCIENCE
(2022)
Article
Chemistry, Organic
Enshen Zhang, Chen Chen, Xueling Wang, Jian Wang, Yongjia Shang
Summary: An efficient palladium-catalyzed reaction has been developed for the construction of spirooxindoles containing E-exocyclic double bonds. This reaction exhibits broad functional group tolerance and excellent chemo- and E/Z selectivities.
ORGANIC CHEMISTRY FRONTIERS
(2022)
