Article
Chemistry, Organic
Tian Ye, Jinjin Zhao, Wan-Xin Zheng, Junmin Zhang, Zhijuan Wang, Feng-Lian Zhang
Summary: A silyl radical-triggered radical addition-translocation-cyclization (RATC) process has been developed to synthesize structurally diverse silicon-incorporated indolines. The reaction involves silyl radical addition, 1,5-hydrogen atom transfer (HAT), and cyclization, leading to the formation of indoline framework. The substituents attached to the radical center can influence the subsequent reactions, including exclusive hydrogen atom transfer, radical 1,4-silyl migration, and oxidation/deprotonation process. These chemo-divergent reactions provide easy access to silicon-modified indolines from simple starting materials.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Multidisciplinary
Qing Wang, Sen-Lin Wang, Jin-Bao Fan, Guang-Yao Zeng, Ying-Jun Zhou, Xu Deng
Summary: Here, we report the first example of both intra- and intermolecular [2+2] cycloaddition reactions between electron-rich indoles and unactivated aryl alkynes. This reaction is promoted by the combination of Fe(NO3)(3) and HNO3, providing efficient and selective access to various functionalized cyclobutene-fused indolines from readily available starting materials, using cheap catalysts and simple operations.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Multidisciplinary
Zhiguo Zhang, Xiaoqing Song, Guofeng Li, Xiang Li, Dan Zheng, Xuna Zhao, Huanran Miao, Guisheng Zhang, Lantao Liu
Summary: This study reports a novel reaction method for the rapid synthesis of polycyclic spiroindolines, containing multiple stereocenters including a quaternary stereocenter. A novel azaphospholidine-containing spiroindoline compound is synthesized for the first time, potentially of interest in synthetic and medicinal chemistry research.
CHINESE CHEMICAL LETTERS
(2021)
Article
Chemistry, Organic
Bruce A. L. Sacchelli, Bianca C. Rocha, Leandro H. Andrade
Summary: An ultrafast methodology utilizing microwave irradiation was employed for the first time to construct novel highly functionalized 2-quinolinones from N-(o-ethynylaryl)-acrylamides (1,7-enynes). The method involved six key consecutive reactions, including a diastereoselective step, to achieve good overall yield of 2-quinolinone-fused gamma-lactones (up to 46%; 10 s).
Article
Chemistry, Organic
Xu-Lun Huang, Yuan-Zheng Cheng, Shu-Li You
Summary: An efficient method for the synthesis of methylene-unsubstituted cyclopropane-fused indolines has been developed. The reaction involves photoredox catalysis and dearomative cyclopropanation of indole derivatives. A wide range of indole derivatives with various functional groups were successfully converted to the desired products in moderate to excellent yields under mild conditions. Asymmetric cyclopropanation was also achieved with good yield and diastereoselectivity, and subsequent removal of the chiral auxiliary produced enantioenriched alcohols. The synthetic value of this reaction was demonstrated through large-scale reactions and derivatization of the products.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Physical
Sarah B. Pawley, Allyssa M. Conner, Humair M. Omer, Donald A. Watson
Summary: General conditions for the Hiyama-Denmark cross coupling of tetrasubstituted vinyl silanes and aryl halides are reported, enabling the coupling of unactivated vinyl silanes and displaying high stereospecificity. This important discovery simplifies the reaction procedure and reduces the use of toxic additives.
Article
Chemistry, Physical
Rahul K. Shukla, Atul K. Chaturvedi, Chandra M. R. Volla
Summary: A Pd(II)-catalyzed directed, regio-controlled hydroheteroarylation of unactivated alkenes has been developed for the construction of gamma-heteroaryl-substituted carbonyl compounds. The methodology is operationally simple and compatible with a variety of nucleophiles to deliver structurally divergent heterocyclic skeletons. This approach also demonstrated synthetic utility in gram-scale synthesis, directing group removal, and late-stage modification of drugs and natural products.
Article
Chemistry, Organic
Linpeng Liu, Yanyu Jian, Weigao Hu, Shaohu Zhao, Zhang-Jie Shi, Nicklas Selander, Taigang Zhou
Summary: A method for radical cyclization and ring-opening of oxime esters with diselenides has been developed. Both Ni(0) and Fe(ii) catalysts can be used for the selenylation of olefin-containing and cyclic oxime ester derivatives. Using this method, a variety of functionalized pyrrolines and alkyl nitriles can be synthesized in good yields. Additionally, a mechanism involving iminyl radical and carbon-centered radical intermediates has been proposed.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Physical
Yong-Liang Su, Geng-Xin Liu, Luca De Angelis, Ru He, Ammar Al-Sayyed, Kirk S. Schanze, Wen-Hao Hu, Huang Qiu, Michael P. Doyle
Summary: This study demonstrates the efficient generation of functionalized derivatives through photocatalyzed multicomponent reactions using nitrogen aromatic heterocycles, alkenes, and diazo compounds. The reaction shows high functional group tolerance and exacting regioselectivities. Mechanistic studies, including photophysical measurements, provide insights into this radical cascade reaction.
Article
Chemistry, Multidisciplinary
Xian Luo, Meng-Meng Xu, Xiao-Ping Xu, Shun-Jun Ji
Summary: An NBS-induced intramolecular annulation of 3-(1H-indol-3-yl)-N-alkoxypropanamide was described. The reaction proceeded efficiently under mild conditions with the assistance of a base. The influence of C2 substituents on the indole ring in 3-(1H-indol-3-yl)-N-alkoxypropanamide was studied, and practical protocols for the synthesis of fused- and spirocyclic indoline compounds were established using C2-methyl- and C2-phenyl-3-(1H-indol-3-yl)-N-alkoxypropanamide as templates.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Xiang Chen, Jun Jiang, Xiao-Jun Huang, Wei-Min He
Summary: An electrochemical oxidative strategy for the synthesis of benzoxazines without transition-metal catalysts and external oxidants is described. Olefinic amides can be transferred to difluoromethylated benzoxazines with up to 87% yield via oxydifluoromethylation using CF2HSO2Na as the reagent in an undivided cell.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Multidisciplinary
Wan-Jie Wei, Lei Zhan, Cai-Na Jiang, Hai-Tao Tang, Ying-Ming Pan, Xian-Li Ma, Zu-Yu Mo
Summary: A mild and efficient electrochemical oxidative strategy was developed for the selective construction of alkoxylated 4H-3,1-benzoxazines and indolines from a single substrate. The protocol exhibits high atom efficiency and does not require transition metals or oxidants. Using a simple undivided cell, 40 examples of benzoxazines and indolines were synthesized from various olefinic amides and alcohols. This radical cascade reaction provides a facile method for one-step construction of C-O bonds. Additionally, most of the compounds showed good inhibitory activity against tumor cell lines.
Article
Chemistry, Multidisciplinary
Chao Liu, Xiangwen Tan, Lingzhi Zhan, Yaru Jing, Wanqing Wu, Zhuofeng Ke, Huanfeng Jiang
Summary: A novel and efficient strategy for synthesizing fused benzo-aza-oxa-[5-6-5] tetracycles with high yields and diastereoselectivities has been demonstrated. This strategy involves the synthesis of functionally divergent anilines and 3-butenoic acid with five chemical bonds constructed. Control experiments and DFT calculations were performed to support the proposed mechanism.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Applied
Pei-Pei Xu, Su-Ge Xin, Xue Li, Cui Liang, Dong-Liang Mo
Summary: We developed a copper(II)-catalyzed [3+2] cycloaddition reaction between N-aryl-alpha,beta-unsaturated nitrones and disubstituted allenoates to prepare a variety of [1,3]oxazino[3,2-a]indolines and dihydropyrido[1,2-a]indolines in moderate to excellent yields. Mechanistic studies revealed the kinetic preference for [1,3]oxazino[3,2-a]indoline and the thermodynamic preference for dihydropyrido[1,2-a]indoline. The reaction can be easily scaled up and chiral dihydropyrido[1,2-a]indoline can be obtained using a chiral auxiliary. The method demonstrates broad substrate scope, good functional group tolerance, and high diastereoselectivity, making it highly significant.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Yin-Long Lai, Shao-Xi Yan, Sheng-Ling Zhang, Yu-Hong Huang, Ru-Xin Hu, Yang-Chong Chen, Jian-Min Luo, Jianxiao Li
Summary: A reliable and efficient palladium-catalyzed cascade cyclization/alkylation reaction of oxime ethers with unactivated alkenes is reported, yielding a variety of structurally diverse isoxazole derivatives in moderate to good yields with excellent functional group compatibility. Ionic liquid [Aeim]Br serves as an environmentally friendly solvent and an accelerating agent, providing excess bromine source to eliminate bromomethane from oxime ethers. Moreover, the use of chain-walking strategy enables rapid generation of molecular complexity from readily available starting materials in organic synthesis.
CHEMISTRY-AN ASIAN JOURNAL
(2022)
Article
Biochemistry & Molecular Biology
Bo-Kai Fang, Chia-Yen Dai, Scott Severance, Chi-Ching Hwang, Chien-Hui Huang, Sin-Yu Hou, Bao-Lin Yeh, Ming-Mao Gong, Yun-Hao Chou, Jeh-Jeng Wang, Tzu-Pin Wang
Summary: This study reports the synthesis of two fluorescence chemical probes capable of quantifying PON1 lactonase activity. One of the probes showed outstanding reactivity and specificity based on reaction analysis and spectroscopic studies. The assay based on this probe was successfully used to determine PON1 activity in human sera.
Article
Multidisciplinary Sciences
Mohana Reddy Mutra, Jeh-Jeng Wang
Summary: This paper presents a method for the cleavage, migration, and functionalization of C(sp)-N bonds in ynamides under blue LED light without the use of metals or additives. This method has important implications in the synthesis of specific compounds.
NATURE COMMUNICATIONS
(2022)
Article
Chemistry, Applied
Mohana Reddy Mutra, Yu-Ting Chen, Jeh-Jeng Wang
Summary: We have developed a photoinduced sulfonyl radical-triggered cyclization of 1,6-dynes without metals, oxidants, or additives. The reaction forms three new bonds (-SO2-C, C-C, and C-I/C-Se-) under mild conditions with excellent selectivity. The conversion is economically and atomically efficient, and can be easily scaled up. Mechanistic studies reveal that the reaction proceeds through a radical pathway. Subsequent synthetic transformations of the products result in various substituted compounds. Notably, a selective C-C single bond cleavage with boronic acid insertion was observed under Suzuki reaction conditions.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Organic
Ajithkumar Arumugam, Pushbaraj Palani, Mageshwari Anandan, Venkatramaiah Nutalapati, Gopal Chandru Senadi
Summary: Highly functionalized quinazolin-4(3H)-ones were synthesized from reactions of N-aryl-2-aminobenzamides with trialkylamines under photocatalytic conditions using eosin Y as a catalyst. The reaction was mild and carried out in aqueous acetonitrile, showing a broad substrate scope. Mechanistic studies revealed the electron-donor nature of the intermediate 2,3-dihydroquinazolin-4(1H)-one (3') in the photocatalytic cycle, leading to the formation of 2,3-disubstituted quinazolin-4(3H)-ones (3). This methodology was also successfully extended to the synthesis of benzo [4,5] imidazole[1,2-c] quinazolines and 3 aa on a large scale, as well as the CNS depressant drugs methaqualone (3 la) and mecloqualone (3 pa).
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Biochemical Research Methods
Dasameswara Rao Kavitapu, Jayanti Naga Sri Rama Chandra Murty, Arthanareeswari Maruthapillai, Gopal C. Senadi, Sudarshan Mahapatra
Summary: A reverse phase HPLC method using a Kinetex C18 column with a gradient elution of buffer and acetonitrile was developed for the quantification of Dasatinib (DST) and its related impurities in pharmaceuticals. The method provided good separation between impurities, and stability indicating capability was demonstrated through degradation studies. Two major impurities were identified and characterized using high-resolution mass spectrometry, nuclear magnetic resonance spectroscopy, and Fourier transform infrared spectroscopy. The analytical HPLC method was validated according to ICH guidelines.
JOURNAL OF CHROMATOGRAPHIC SCIENCE
(2023)
Article
Chemistry, Organic
Swetha Sathyendran, Kesavan Muthu, Karthick Govindan, Nian-Qi Chen, Wei-Yu Lin, Gopal Chandru Senadi
Summary: A FeCl3-catalyzed decyanation of alpha-aminonitriles followed by a [4 + 2] annulation with terminal alkynes has been developed for the synthesis of 2,4-diaryl quinolines. The reaction showed good tolerance towards various aniline, aldehyde, and arylacetylene derivatives, providing moderate to good yields of the desired products. Control experiments suggested a nonradical pathway involving Povarov-type [4 + 2] annulation from an in situ generated iminium species. The method demonstrated the capability for gram-scale synthesis, continuous-flow process, and successful application with styrene.
Article
Chemistry, Organic
Ariprasanth Ramalingam, Gopal Chandru Senadi
Summary: Here, we report a simple and straightforward magnetic heterogeneous catalytic approach using H2O as an environmentally friendly solvent to synthesize benzimidazole and quinoxaline scaffolds from o-phenylene diamines and primary amines. The method has the advantages of high yields and reusable catalyst, making it suitable for industrial synthesis.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Materials Science, Multidisciplinary
Bharathi Kannan Raja, Abigail Philips, Sanmugapriya Ravi, Monisha Ravi, Athulya S. Palakkal, Renjith S. Pillai, Gopal Chandru Senadi, J. Arockia Selvi
Summary: In this study, aza-heterocyclic compound 3-phenylquinazolin-4(3H)-one (3pq) was synthesized using a renewable biomass source, and its structure was confirmed using 1H NMR, 13C NMR, and FT-IR spectroscopic techniques. The inhibitory activity of 3pq against corrosion of MS in 1 N HCl solution was examined using weight loss measurements, potentiodynamic polarization study, and electrochemical impedance spectroscopy. Various characterization techniques such as SEM, AFM, UV-Vis, XPS, and FTIR were employed to analyze the surface morphology, formation of a protective film, complex formation, and effective adsorption of 3pq on the MS surface. Computational studies based on DFT were also conducted to investigate the adsorption ability of 3pq on the MS surface.
MATERIALS CHEMISTRY AND PHYSICS
(2023)
Review
Chemistry, Organic
Swetha Sathyendran, Gopal Chandru Senadi
Summary: Functional group transformation of nitriles is an important research topic in synthetic chemistry, with potential applications in the synthesis of ketones and amides. This article provides an overview of studies on the oxidative decyanation of nitriles and alpha-aminonitriles to obtain corresponding ketones and amides.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Babasaheb Sopan Gore, Jeh-Jeng Wang
Summary: Here, we report a photoinduced energy-transfer catalysis reaction of tethered conjugated dienes, enabling the synthesis of bridged cyclopropanes. This single-step reaction efficiently generates complex tricyclic compounds with multiple stereocenters from readily accessible starting materials. The reaction demonstrates a broad substrate scope, atom-economy, excellent selectivity, and satisfactory yield, including facile scale-up synthesis and synthetic transformation. An in-depth mechanistic study reveals that the reaction proceeds via an energy-transfer pathway.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Mohana Reddy Mutra, Jing Li, Jeh-Jeng Wang
Summary: We efficiently synthesized tetrasubstituted olefins in a highly selective and stereoselective manner using sulfonyl iodides from ynamides and internal alkynes under blue LED irradiation in just a few minutes. This metal-free, user-friendly, and environmentally friendly approach showed broad applicability, as demonstrated by the successful gram-scale experiment and subsequent transformation of the sulfonyl-iodinated products into diverse compounds.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Babasaheb Sopan Gore, Lin-Wei Pan, Jun-Hao Lin, Yi-Chi Luo, Jeh-Jeng Wang
Summary: Here, we report a visible light-promoted intramolecular radical cascade reaction for the construction of fluorenol and naphthalene-fused cyclopropyl carbaldehyde derivatives. This method offers mild reaction conditions, a broad substrate scope, excellent step efficiency, and scalability, without the need for external chemical oxidants. The novelty of this protocol was demonstrated by synthesizing chrysene analogs and performing late-stage functionalizations.
Article
Chemistry, Multidisciplinary
Pushbaraj Palani, Ajithkumar Arumugam, Dineshkumar Raja, Kesavan Muthu, Gopal Chandru Senadi
Summary: A mild and inexpensive approach to synthesizing a series of 1,4-diketones in moderate to excellent yields via 1,2-oxo alkylation has been developed using fluorescein as a photocatalyst and air as an oxidant. The key features of this method include a wide range of substrate scope, good functional group tolerance, the synthesis of unsymmetrical 1,4-dicarbonyls, late-stage functionalization of thymol and ibuprofen derivatives, as well as the expansion to N-, O-, and S-containing heterocycles with 5- and 6-members.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Mathiyazhagan Sivanantham, Abigail G. Jennifer, Elumalai Varathan, Mohankumar Ramasamy, Gopal Chandru Senadi
Summary: An iodine-mediated radical cyclization method was developed for the synthesis of iodo-sulphonylated-succinimide derivatives. The method offers metal-free conditions, broad functional group tolerance, column chromatography-free purification, high stereoselectivity (E isomer), shorter reaction times, and cascade construction of multiple new bonds (C-S, C-I, and C-C).
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Ariprasanth Ramalingam, Elavarasan Samaraj, Selvaraj Venkateshwaran, Sakkarapalayam Murugesan Senthilkumar, Gopal Chandru Senadi
Summary: Earth-abundant transition metal dichalcogenides (TMDs), especially molybdenum disulfide (MoS2), have been proven to be effective catalysts for improving the catalytic performance of heterogeneous catalysis in organic functional group conversion chemistry. In this study, a new method achieved 84% phase enrichment of 1T-MoS2 in aqueous medium, which provides the possibility for industrial applications. Furthermore, the catalytic behavior of 1T-MoS2 in the reduction of aromatic nitro compounds into aromatic amines was realized, showing high reproducibility, recyclability, and short reaction times.
NEW JOURNAL OF CHEMISTRY
(2022)
