Article
Chemistry, Organic
Manisha, Shiv Shankar Gupta, Ankit Kumar Dhiman, Upendra Sharma
Summary: An efficient Rh-catalyzed method has been developed for selective C7 halogenation of N-pyrimidyl indolines, producing corresponding halides in good to excellent yields. The strategy demonstrates broad substrate scope, excellent regioselectivity for C7 functionalization of indolines, and feasibility at gram scale level. Various control experiments were conducted to understand the reaction pathway, and the applicability of the methodology was demonstrated by synthesis of indoles and post-transformation of the C7 halogenated indolines into different valuable molecules.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Applied
Shi-Yi Zhuang, Yong-Xing Tang, Cai He, Xiang-Long Chen, Wei-Jian Xue, Yan-Dong Wu, An-Xin Wu
Summary: A novel synthetic method was developed using copper catalysis to achieve site-selective C5-dicarbonylation of anthranils, leading to the synthesis of 1,2-dicarbonyl compounds. This process represents the first example of implementing C5-dicarbonylation of anthranils, involving oxidative Csp(3)-H/Csp(2)-H cross-coupling reaction and thermolytic N-O bond cleavage.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Organic
Mohit Kumar, Anushka Rastogi, Raziullah, Ashfaq Ahmad, Manoj Kumar Gangwar, Dipankar Koley
Summary: A copper-catalyzed method for the synthesis of N-arylated sulfoximines via dual N-H/C-H activation has been developed. This method shows good compatibility with various commonly used functional groups as well as medicinally relevant scaffolds.
Article
Chemistry, Organic
Yunkai Shi, Chao Chen, Yaxi Yang, Bing Zhou
Summary: The Rh(III)-catalyzed C7-selective C-H activation/annulation of indolines with 1,3-enynes provides access to various privileged 1,7-fused indolines with an all-carbon quaternary stereogenic carbon center. The resulting products can be easily transformed into 1,7-fused indoles, expanding the C-7 derivatization of indoles and demonstrating the synthetic utility of this methodology.
TETRAHEDRON LETTERS
(2021)
Article
Chemistry, Organic
Weiqiang Chen, Chao-Yi Li, Hui-Jing Li, Yan-Chao Wu
Summary: The research developed a new method using [RhCp*Cl-2](2)/AgSbF6 system for C2-amination reaction between ketoximes and anthranils. Piv(2)O as a promoter played a key role in catalytic activity, and the oxime unit effectively activated the aryl C-H bond.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Nan Ma, Zheyuan Liu, Jianhui Huang, Yanfeng Dang
Summary: Density functional theory calculations have revealed the mechanism and origins of the reactivity and regioselectivity of the Cp*Ir(iii)/Cp*Rh(iii)-catalyzed allylic C-H amidation. The rate-determining step is found to be the C-H activation, which differs between the Cp*Ir(iii) and Cp*Rh(iii) systems, affecting their reactivity and regioselectivity. The insights provided by this study will be valuable for the development of transition metal-catalyzed selective C-H amination reactions.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Organic
Tapasi Chand, Laxmikanta Khamari, Saptarshi Mukherjee, Manmohan Kapur
Summary: This study reports the direct formation of a C-N bond at the ortho-position of naphthalene monoimides (NMI) and perylenemonoimides (PMI) using dioxazolones as the amide source. This method allows direct access to ortho-amino NMI and PMI through an amidation and deprotection sequence. The incorporation of pivalamide groups at the ortho-position of NMI and PMI improves the quantum yield and fluorescence lifetime.
Article
Chemistry, Organic
Hui Xie, Jia-Lin Song, Chun-Yong Jiang, Yan-Xia Huang, Jun-Yi Zeng, Xu-Ge Liu, Shang-Shi Zhang, Fan Yang
Summary: This new method of thioether-directed acyloxylation of arenes through Cp*Rh(iii)-catalyzed C-H activation shows high functional group compatibility and broad substrate scope. Preliminary mechanistic studies have been conducted, proposing a tentative reaction mechanism for this novel process.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Organic
Jia-Lin Song, Shao-Yong Chen, Lin Xiao, Xiao-Ling Xie, Yi-Chuan Zheng, Shang-Shi Zhang, Bing Shu
Summary: A method for the preparation of N-aryl amides has been established using Rh(III)-catalyzed C(sp(2))-N cross-coupling reactions. This efficient and straightforward catalytic approach has a broad substrate scope, good functional group compatibility, high yields, and is suitable for late-stage modification of drug molecular structures.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Zhong-Wei Hou, Ding-Jin Liu, Peng Xiong, Xiao-Li Lai, Jinshuai Song, Hai-Chao Xu
Summary: This study reports a site-selective electrochemical amination reaction that can convert benzylic C-H bonds into C-N linkages without the need for external oxidants or metal catalysts. The success lies in using HFIP as a co-solvent to modulate the oxidation potentials of the substrate and product, avoiding overoxidation of the latter.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Inorganic & Nuclear
Juping Wang, Rongxing Xiao, Kangcheng Zheng, Li Qian
Summary: The computational study examined the mechanism and site-selectivity for Fe-catalyzed azaindoline formation from 1,2,3,4-tetrazole. It was found that the aliphatic H-atom abstraction (HAA) and electrophilic aromatic substitution (EAS) steps play a key role in determining the sp(3) vs. sp(2) C-H amination site-selectivity, with Fe-catalysis favoring sp(3) C-H amination due to steric congestion.
DALTON TRANSACTIONS
(2021)
Article
Chemistry, Organic
Weiqiao Lan, Jiatong Zhu, Buweihailiqiemu Abulaiti, Genyuan Chen, Zhihao Zhang, Nan Yan, Jie-Ping Wan, Xiaomei Zhang, Lihua Liao
Summary: An efficient zinc-catalyzed amination reaction has been developed for the para-selective amination of free anilines and free phenols with quinoneimides, leading to C-N bond formation via a 1,6-addition pathway. This protocol not only offers a promising approach for constructing structurally diverse p-phenylenediamine compounds with excellent yields, but also extends the application of the quinoneimide-involved 1,6-addition reaction.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Eunjae Chung, Suho Kim, Amitava Rakshit, Pargat Singh, Jaewook Park, Taejoo Jeong, In Su Kim
Summary: In this study, the rhodium(III)-catalyzed C8-spiroannulation of 1-aminonaphthalenes with maleimides is investigated. The resulting C8-alkenylated 1-aminonaphthalenes can further react with nucleophilic 1-amino groups through intramolecular aza-Michael reaction, leading to the formation of spirofused tetracyclic frameworks. This method demonstrates a broad substrate scope and compatibility with various functional groups.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Review
Chemistry, Multidisciplinary
Bijin Li, Mazen Elsaid, Haibo Ge
Summary: C(sp(3))-H functionalization is an important method to increase molecular complexity. Despite the initial challenges of inertness and high bond-dissociation energies, these hurdles can be overcome through selective strategies, leading to efficient construction of C-C and C-X bonds. This review discusses transition-metal-catalyzed site-selective gamma- and delta-C(sp(3))-H functionalization reactions and explores their applications in late-stage functionalization of medicinal compounds and construction of complex molecules of medicinal importance.
Article
Chemistry, Organic
Carlota Giron-Elola, Ibon Sasiain, Rosaliia Sanchez-Fernandez, Elena Pazos, Arkaitz Correa
Summary: A cross-dehydrogenative coupling reaction of Tyr-containing peptides and estrogens with heteroarenes was developed, allowing for the formation of C-N bonds. This scalable and air-tolerant oxidative coupling reaction has operational simplicity and enables the attachment of phenothiazines and phenoxazines in phenol-like compounds. Incorporation of the Tyr-phenothiazine moiety into a Tb(III) metallopeptide serves as a sensitizer for the Tb(III) ion, providing a new tool for the design of luminescent probes.
Article
Biochemistry & Molecular Biology
Hee Jung Kim, Dong Uk Im, Gia Cac Chau, Neeraj Kumar Mishra, In Su Kim, Sung Hee Um
Summary: In this study, a newly synthesized indole derivative, CF3-allylated indole, was found to effectively inhibit adipogenesis by regulating PKA/AMPK signaling in the early stage of adipocyte differentiation. These findings suggest the potential of CF3-allylated indole in controlling initial adipocyte differentiation in metabolic disorders such as obesity.
CHEMICO-BIOLOGICAL INTERACTIONS
(2022)
Article
Biochemistry & Molecular Biology
Younggyu Kong, Pulla Reddy Boggu, Gi Min Park, Yeon Su Kim, Seong Hwan An, In Su Kim, Young Hoon Jung
Summary: The total synthesis of eliglustat, an approved drug for non-neurological Gaucher disease, starting from 1,4-benzodioxan-6-carbaldehyde is described. The synthesis involves Sharpless asymmetric dihydroxylation and diastereoselective amination steps, with chlorosulfonyl isocyanate as a key reactant.
Article
Chemistry, Organic
Suho Kim, Heon Kyu Park, Ju Young Kang, Neeraj Kumar Mishra, In Su Kim
Summary: The hydrazide-assisted rhodium(III)-catalyzed cross-coupling reactions of N-arylphthalazinones and N-arylindazolones with vinylene carbonate were reported, providing direct access to tetracyclic hydroxycinnolines. The reactions exhibited complete site-selectivity and functional group compatibility.
SYNTHESIS-STUTTGART
(2022)
Article
Chemistry, Organic
Yeon Su Kim, Pulla Reddy Boggu, Younggyu Kong, Gi Min Park, In Su Kim, Young Hoon Jung
Summary: The synthesis of a-1-C-propyl-3,6-di-epi-nojirimycin and Polyhydroxyindolizidine alkaloids from readily available a-methyl-D-mannopyranoside is described. The key step in this process involves a regioselective and diastereoselective amination of the anomeric acetal functionality using chlorosulfonyl isocyanate (CSI).
Article
Chemistry, Multidisciplinary
Ju Young Kang, Suho Kim, Junghyea Moon, Eunjae Chung, Jaeyoung Kim, So Young Kyung, Hyung Sik Kim, Neeraj Kumar Mishra, In Su Kim
Summary: The rhodium(III)-catalyzed 1,4-addition reaction of maleimides with N-aryl indazol-3-ols, disclosed in this study, provides succinimide-bearing indazol-3-ol scaffolds with complete regioselectivity and good functional group tolerance. The versatility of this protocol is demonstrated by the use of drug-molecule-linked and fluorescence probe-linked maleimides.
Article
Biochemistry & Molecular Biology
Prasanta Dey, Amit Kundu, Ha Eun Lee, Babli Kar, Vineet Vishal, Suvakanta Dash, In Su Kim, Tejendra Bhakta, Hyung Sik Kim
Summary: The extract of Molineria recurvata exhibits protective effects on nephropathy in diabetic rats by suppressing inflammation and oxidative stress.
Article
Biochemistry & Molecular Biology
Gi Min Park, Sun Ju Kong, Jae Hyeon Park, Ji Eun Kang, Sung Hwan An, Hyung Sik Kim, In Su Kim, Pulla Reddy Boggu, Young Hoon Jung
Summary: A concise synthesis of ent-conduramine C-1 and its derivatives has been achieved using commercially available D-ribose. The key steps in the synthesis involved regioselective and diastereoselective amination, chelation-controlled carbonyl addition, and intramolecular olefin metathesis. The synthesized compounds were evaluated for their inhibitory activity against alpha-glucosidase, with derivatives 18 and 19 showing stronger inhibition than acarbose.
CARBOHYDRATE RESEARCH
(2023)
Article
Chemistry, Organic
Haritha Sindhe, Nehanaz Saiyed, Akshay Kamble, Malladi Mounika Reddy, Amardeep Singh, Satyasheel Sharma
Summary: This study reports an efficient metal-free chemodivergent protocol for the synthesis of 1-substituted 9H-pyrrolo[1,2-a]indole derivatives using catalytic amounts of Lewis acid/Bronsted acid conditions. The fine-tuning of catalyst and solvent system allows for the introduction of trifluoromethyl, trifluoroethylcarboxylate, or carboxylic acid substituents on the C1-position of the derivatives in situ.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Nayoung Ko, Jeonghyun Min, Junghyea Moon, Nuraimi Farwizah Ismail, Kyeongwon Moon, Pargat Singh, Neeraj Kumar Mishra, Wonsik Lee, In Su Kim
Summary: The rhodium(III)-catalyzed conjugate addition of fi-trifluoromethylated enones with quinoline N-oxides for the site-selective incorporation of a trifluoromethyl group into biologically active molecules and pharmaceuticals has been demonstrated. The reaction shows excellent functional group tolerance and synthetic applicability, making it a valuable tool for gram-scale experiments and coupling product transformations.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Oncology
Jong Seung Lim, So Young Kyung, Yukyoung Jeon, In Su Kim, Jong Hwan Kwak, Hyung Sik Kim
Summary: The study investigated the HDAC inhibitory and anticancer activities of ACT-3 in MCF-7 human breast cancer cells. ACT-3 and SAHA increased acetylated histone H3 levels and reduced HDAC1 and HDAC3 levels. ACT-3 inhibited cell proliferation, induced cell cycle arrest and apoptosis, and increased autophagic cell death in MCF-7 cells. ACT-3 also activated the ERK pathway to inhibit cell growth and promote apoptosis in MCF-7 cells.
Article
Chemistry, Organic
Amardeep Singh, Monika Diwaker, Akshata Thakur, Khemchand Surana, Manjeet Chopra, Hemant Kumar, Satyasheel Sharma
Summary: O-Carbamate assisted Palladium (II) catalyzed regioselective C-H acylation of coumarins at C-6 position with arylglyoxylic acids was achieved. The synthesized molecules showed anti-inflammatory activity, with compound 3ia being the most active in inhibiting NF-kB expression. Further studies demonstrated that carbamate-based C-6 acylated coumarin derivatives inhibited the nuclear translocation of p65, mitigating the activation of the inflammatory cascade.
Article
Oncology
Chunxue Jiang, Xiaodi Zhao, Taejoo Jeong, Ju Young Kang, Jae Hyeon Park, In Su Kim, Hyung Sik Kim
Summary: Prostate cancer is a serious threat to male health globally, and chemotherapy resistance is a pressing issue. The discovery of novel molecules and chemotherapy strategies is crucial. This study identified a specific PKM2 inhibitor, compound 3h, and evaluated its anticancer effects through molecular and cellular experiments. The results demonstrated that compound 3h inhibits proliferation of LNCaP cells by inducing apoptosis, autophagy, and inhibiting glycolysis and mitochondrial respiration. This research provides a new approach for the development of novel chemotherapy for prostate cancer.
Review
Chemistry, Organic
Haritha Sindhe, Malladi Mounika Reddy, Karthikeyan Rajkumar, Akshay Kamble, Amardeep Singh, Anand Kumar, Satyasheel Sharma
Summary: Pyridine is a critical heterocyclic scaffold widely used in organic chemistry, medicines, natural products, and functional materials. New methodologies for the direct functionalization of pyridine scaffolds have been developed in the past two decades, including transition-metal-catalyzed C-H functionalization and rare earth metal-catalyzed reactions. This review discusses recent achievements in these areas and explores the underlying mechanisms.
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Haritha Sindhe, Nehanaz Saiyed, Akshay Kamble, Malladi Mounika Reddy, Amardeep Singh, Satyasheel Sharma
Summary: In this study, an efficient metal-free chemodivergent protocol for the synthesis of 1-substituted 9H-pyrrolo[1,2-a]indole derivatives was reported. By fine-tuning the catalyst and solvent system, trifluoromethyl, trifluoroethylcarboxylate, or carboxylic acid substituents can be introduced on the C1-position of these derivatives. The solvent and catalyst interaction were found to be crucial for the catalytic C-F activation in these transformations.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Review
Chemistry, Multidisciplinary
Neeraj Kumar Mishra, Amitava Rakshit, Kyeongwon Moon, Pargat Singh, In Su Kim
Summary: The synthesis and functionalization of privileged nitrogen heterocycles play a central role in drug discovery and material science. Tandem C-H functionalization and intramolecular annulation have gained significant attention for their ability to expedite the construction of heteroaromatic frameworks. While there has been progress in the [3 + 2] dipolar cycloaddition of azomethine imines with pi-unsaturated compounds, the combination of catalytic C-H functionalization and intramolecular cyclization using azomethine imines as both directing groups and dipolar units remains less explored.
BULLETIN OF THE KOREAN CHEMICAL SOCIETY
(2023)
