Article
Chemistry, Organic
Amu Wang, Ya-Zhou Liu, Zhongke Shen, Zeen Qiao, Xiaofeng Ma
Summary: A TEMPO-mediated [3 + 2] annulation-aromatization protocol for the preparation of pyrazolo[1,5-a]pyridines has been developed, offering good to excellent yields with high and predictable regioselectivity. The modification of marketed drugs and a one-pot three-step gram scale synthesis of a key intermediate for Selpercatinib preparation have been demonstrated.
Article
Chemistry, Applied
Zemin Qin, Renchao Ma, Shenpeng Ying, Fanzhu Li, Yongmin Ma
Summary: 2-Mono- or 2,3-disubstituted pyrimido[1,2-b]indazoles were synthesized successfully through a (3+2+1) three-component cyclization reaction. The reaction exhibited good tolerance towards different substitution patterns and aromatic/aliphatic ketones, and could be conducted in air.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Organic
Brianna M. Bembenek, Maya M. S. Petersen, Julia A. Lilly, Amber L. Haugen, Naomi J. Jiter, Andrew J. Johnson, Ethan E. Ripp, Shelby A. Winchell, Alisha N. Harvat, Caitlin McNulty, Sierra A. Thein, Abbigail M. Grieger, Brandon J. Lyle, Gabriella L. Mraz, Abigail M. Stitgen, Samuel Foss, Merranda L. Schmid, Joseph D. Scanlon, Patrick H. Willoughby
Summary: This study focuses on the generation of complex molecules with diverse functionality using two aryne intermediates. By synthesizing aryl phosphonates through specific methods, the research demonstrates the usefulness of these compounds in medicinal chemistry and materials science. Moreover, the regioselectivity of aryne trapping reactions can be tuned by simply changing the solvent, showcasing the versatility and control of the reaction process.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Ahmad Daher, Asmae Bousfiha, Iogann Tolbatov, Cleve D. Mboyi, Helene Cattey, Thierry Roisnel, Paul Fleurat-Lessard, Muriel Hissler, Jean-Cyrille Hierso, Pierre-Antoine Bouit, Julien Roger
Summary: A new class of aza-polyaromatics was synthesized in a straightforward manner. Starting from fluorinated s-tetrazine, a cyclization process with azide led to the formation of tetrazo[1,2-b]indazole or bis-tetrazo[1,2-b]indazole (cis and trans conformers). The subsequent N-directed palladium-catalyzed ortho-C-H bond functionalization allowed the introduction of halides or acetates. The physicochemical properties of these compounds were investigated using experimental and theoretical methods, revealing solid-state pi-stacking, low reduction potential, absorption in the visible range up to the near-infrared, and intense fluorescence depending on the molecular structure.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Abdul Qaiyum Ramle, Chee Chin Fei, Edward R. T. Tiekink, Wan Jefrey Basirun
Summary: A new series of pyrimido[1,2-b]indazoles containing indolenine moieties was synthesized with up to 94% yield through a simple condensation reaction. This method allows for the versatile formation of a pyrimidine ring, compatibility with a wide range of substrates, and easy synthesis, providing opportunities in drug development and materials science.
Article
Chemistry, Organic
Rahul N. Gaykar, Shiksha Deswal, Avishek Guin, Subrata Bhattacharjee, Akkattu T. Biju
Summary: This study demonstrates the synthesis of 2,4,5-trisubstituted oxazoles through a transition-metal-free chemical reaction under mild conditions. The desired products were obtained through a series of reaction steps.
Article
Chemistry, Organic
Dmitry S. Ivanov, Elvira R. Zaitseva, Alexander Yu. Smirnov, Alexey V. Nizovtsev, Nadezhda S. Baleeva, Mikhail S. Baranov
Summary: A simple procedure was developed to synthesize 2H-pyrido[3,4-c][1,2]benzoxazine-2,4(3H)-diones from o-fluorophenyl-substituted 6-oxo-6H-1,2-oxazine-3-carboxylates using primary amines. The reaction followed a previously described mechanism for the formation of 3-(hydroxyimino)pyridine-2,6-diones, followed by intramolecular nucleophilic substitution to form the 1,2-oxazine ring.
CHEMISTRY OF HETEROCYCLIC COMPOUNDS
(2023)
Article
Chemistry, Organic
Yangang Wu, Wenbo Cai, Lulu Yu, Junbiao Chang, Chuanjun Song
Summary: A literature-unprecedented three-component aryne coupling reaction has been developed, utilizing pyrroline, imine, dihydroisoquinoline, imidazoline or oxazoline as nucleophiles and acrylonitrile as a third component, which acts as both a proton donor and a nucleophile.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Zemin Qin, Ruiqin Zhang, Shenpeng Ying, Yongmin Ma
Summary: A simple and efficient method for the synthesis of pyrimido[1,2-a]benzimidazoles and pyrimido[1,2-b]indazoles has been developed using 2-aminobenzimidazoles/3-aminoindazoles, alkynes, and N,N-dimethylaminoethanol as reactants, and FeCl3 as a catalyst. The reaction shows good tolerance and can be applied to the construction of biologically active compounds.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Dmitry Osipov, Kirill S. Korzhenko, Daria A. Rashchepkina, Alina A. Artemenko, Oleg P. Demidov, Vadim A. Shiryaev, Vitaly A. Osyanin
Summary: The study focused on the [3 + 2]-cycloaddition of various N,N-cyclic azomethine imines to 3-nitrobenzofurans, achieving dearomatization and extending the process to related molecules. Mechanistic insights were obtained through DFT calculations, explaining the experimentally determined limitations of the method.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Organic
Madavi S. Prasad, Sankar Bharani, Murugesan Sivaprakash, Prabha Vadivelu, Durairajan Siva Sundara Kumar, L. Raju Chowhan
Summary: This study describes the first report on using N-2,2,2-trifluoroethylisatin ketimine as a 1,2-dipolarophile for [3+2]-addition and the first asymmetric synthesis of N-2,2,2-trifluoroethylspirothiazolidine oxindoles. The reaction between N-2,2,2-trifluoroethylisatin ketimine and 1,4-dithiane-2,5-diol, utilizing organocatalysis, provided an array of N-2,2,2-trifluoroethylspirothiazolidine oxindoles in excellent yield, enantioselectivity, and diastereoselectivity. Furthermore, the developed methodology demonstrated synthetic utility by transforming optically pure spirothiazolidine into medicinally important spirothiazolidinone and spirothiazolidinone-S-oxide.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Organic
Jih Ru Hwu, Avijit Panja, Nitesh K. Gupta, Wen-Chieh Huang, Yu-Chen Hu, Chun-Cheng Lin, Kuo-Chu Hwang, Wei-Jen Chan, Shwu-Chen Tsay
Summary: The synthesis of optically active 3-pyrrolines through a newly developed domino reaction using a chiral catalyst showed high stereo- and enantio-selectivity, with a single product generated in good yields. The reaction also involved an aryne-induced domino reaction and an unusual 1,4-intramolecular proton transfer, demonstrating high enantiomeric ratios up to 98.5:1.5.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Hemanta Hazarika, Kangkana Chutia, Babulal Das, Pranjal Gogoi
Summary: An aryne-based synthetic protocol has been developed for the synthesis of 3-substituted-3-hydroxy-indolin-2-ones, yielding a wide variety of products in good yields. One of the synthesized compounds has been confirmed by single crystal XRD analysis. Treating the synthesized derivatives with an inorganic base at high temperature leads to an interesting o-arylated product of 1,3-cyclohexandione.
NEW JOURNAL OF CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Feng Jiang, Chunling Fu, Shengming Ma
Summary: This paper describes the cycloisomerization of N-1,3-disubstituted allenyl indoles catalyzed by IPrAuCl/AgSbF6, leading to the formation of pyrido[1,2-a]-1H-indoles. The transfer of chirality from enantio-enriched N-1,3-disubstituted allenyl indoles to optically active pyrido[1,2-a]-1H-indoles was achieved with excellent yields and enantioselectivities. A proposed mechanism based on mechanistic studies and synthetic applications were also demonstrated in the study.
Article
Chemistry, Multidisciplinary
Durgesh Gurukkala Valapil, Priyanka Mishra, Kalyani Jungare, Nagula Shankaraiah
Summary: A facile [3+3] annulation method for the construction of fused a-carboline or indolo[2,3-c]isoquinoline frameworks from easily synthesizable N,N'-cyclic azomethine ylides and 3-diazoindolin-2-imines using a Ru(II) catalyst is reported. This strategy was found to be efficient and effective for the syntheses of a variety of fused polycyclic molecules with a wide substrate scope, mild reaction conditions, and good to excellent yields. In addition, the mechanistic pathway of this transformation has been investigated by performing various control experiments with ESI-MS analyses.
NEW JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Organic
Yantao Liu, Wen Luo, Zhenjie Wang, Yuxin Zhao, Jingjing Zhao, Xuejun Xu, Chaojie Wang, Pan Li
Article
Chemistry, Applied
Jiupeng Liu, Jiaqi Li, Bowen Ren, Yun Zhang, Linyi Xue, Yanying Wang, Jingjing Zhao, Puyu Zhang, Xuejun Xu, Pan Li
Summary: The reactivity of N-tosyl vinylaziridines towards arynes has been demonstrated in mild and transition-metal-free conditions, leading to the formation of 2-(phenanthren-9-yl)ethan-1-sulfamides in moderate to good yields. Selective synthesis of N-H and N-aryl products was achieved using different conditions, involving a cascade process of sequential Diels-Alder reaction, ring-opening aromatization, ene-reaction, and selective N-arylation reaction.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Multidisciplinary
Yantao Liu, Yating Shi, Lanen Wei, Ke Zhao, Jingjing Zhao, Puyu Zhang, Xuejun Xu, Pan Li
Summary: A gold-catalyzed synthesis of polyfluoroalkylated oxazoles from N-propargylamides under visible-light irradiation has been developed, showing excellent compatibility of radicals and gold catalysts. Mechanistic experiments revealed the dual role of polyfluoroalkyl iodides in enhancing compatibility and reactivation of the gold catalyst. Furthermore, PPh3AuNTf2 not only activates N-propargylamide to generate vinyl gold intermediate, but also promotes homolysis of polyfluoroalkyl iodides under blue light irradiation.
CHEMISTRY-AN ASIAN JOURNAL
(2021)
Article
Chemistry, Organic
Yantao Liu, Keyong Zhu, Yuting Kong, Xiao Li, Jie Cui, Yifan Xia, Jingjing Zhao, Shaofeng Duan, Pan Li
Summary: A mild and highly efficient approach to alkyl oxazoles has been reported, utilizing a combination of gold/copper catalysis and copper/photoredox catalysis. Various alkyl oxazoles can be synthesized with good to excellent yields and wide functional-group compatibility under blue-light irradiation. The copper catalyst plays a dual role in accelerating protodeauration of vinyl gold intermediates and enhancing photoredox catalysis in this transformation.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Jiupeng Liu, Shuo Tang, Mengyao Zhao, Jianing Huai, Jingya Yu, Jingjing Zhao, Pan Li
Summary: The reactivity of vinyl epoxides/oxetanes/cyclopropanes towards arynes can lead to the synthesis of various functionalized phenanthrenes under mild conditions. This transition-metal-free cascade process involves a series of Diels-Alder reaction, ring-opening aromatization, and ene reaction. Vinyl epoxides/oxiranes show a preference for Diels-Alder reaction with arynes over nucleophilic attack.
Article
Chemistry, Organic
Jiupeng Liu, Shuo Tang, Shichong Wang, Mengting Cao, Jingjing Zhao, Puyu Zhang, Puyu Li
Summary: A visible-light-induced C-Br bond homolysis of bromomalonates has been developed, providing an efficient approach for the synthesis of carbonylated and hydroxylated benzofurans from 1,6-enynes under mild conditions, without the need for transition metals, photocatalysts, oxidants, or additives. Mechanistic studies suggest an energy-transfer pathway for the C-Br bond homolysis, with atom-transfer radical addition products serving as key intermediates for the generation of carbonylated and hydroxylated benzofurans.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Tao Zhang, Shichong Wang, Dandan Zuo, Jingjing Zhao, Wen Luo, Chaojie Wang, Pan Li
Summary: A palladium-catalyzed carbonylative [5+1] cycloaddition reaction of N-tosyl vinylaziridines with CO has been developed, providing a practical and efficient method for synthesizing different types of δ-lactams. The choice of solvent allows for control over the type of lactam produced. Additionally, this method exhibits excellent step- and atom-economy and shows higher regioselectivity towards [5+1] cycloaddition.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Jiaqi Li, Shichong Wang, Jingjing Zhao, Pan Li
Summary: A visible light-promoted radical-mediated ring-opening/cyclization of vinyl benzotriazoles has been developed for the synthesis of functionalized phenanthridines from alkyl bromides. The readily available and bench-stable vinyl benzotriazoles serve as valuable alternative radical acceptors during the synthesis of phenanthridines.
Article
Chemistry, Organic
Dandan Zuo, Tao Zhang, Jingjing Zhao, Wen Luo, Chaojie Wang, Pan Li
Summary: A palladium-catalyzed regioselective [5 + 1] annulation reaction of vinyl aziridines/epoxides with ClCF2COONa has been developed. This reaction utilizes vinyl aziridines/epoxides as heteroatom-containing five-atom synthons, and ClCF2COONa as a cheap and commercially available source of carbonyl, serving as a difluorocarbene precursor. This protocol provides an efficient and practical method for the synthesis of delta-lactams and delta-lactones in good yields.
Article
Chemistry, Organic
Keyong Zhu, Mengting Cao, Guanzhen Zhao, Jingjing Zhao, Pan Li
Summary: This study developed a method for the visible light-promoted generation of nitrilium ions from diazoacetates and nitriles. The reaction involves the transformation of diazoacetates to free carbenes under visible light, which are then trapped by nitriles to generate nitrilium ions. Nitrilium ions undergo nucleophilic attack on benzotriazoles and carboxylic acids to produce N-imidoylbenzotriazoles and diacylglycine esters in good to excellent yields.
Article
Chemistry, Organic
Yantao Liu, Keyong Zhu, Jingjing Zhao, Pan Li
Summary: This study developed a visible-light photocatalytic regioselective difunctionalization of alkenes with diazo compounds and tert-butyl nitrite, providing an efficient approach to gamma-oximino esters under mild conditions. The transformation not only demonstrated the good compatibility of nucleophilic diazo compounds and electrophilic tert-butyl nitrite, but also revealed the preference of alkyl radicals generated by diazo compounds for addition to alkenes over nitroso radicals.
Article
Chemistry, Multidisciplinary
Keyong Zhu, Xinlong Zhou, Yikun Ren, Linhui Dong, Guanzhen Zhao, Jingjing Zhao, Pan Li
Summary: A visible light-induced carbene reactivity of acceptor diazoalkanes enables the synthesis of difunctionalized ethers from cyclic ethers and various N/O/S nucleophiles.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Jiupeng Liu, Shuo Tang, Huayan Xu, Ruoyu Zhang, Jingjing Zhao, Puyu Zhang, Pan Li
Summary: A visible-light photocatalytic regioselective [2 + 2 + 1] radical annulation reaction of alkenes, tert-butyl nitrite, and gemdihalides has been developed, providing an efficient and practical approach to obtain isoxazolines in good yields under mild conditions. Gem-dihalides serve as C1 synthons, while cheap tert-butyl nitrite acts as an ideal N-O synthon.
Article
Chemistry, Multidisciplinary
Keyong Zhu, Wen-Jing Yu, Xinlong Zhou, Chaogui Xu, Guanzhen Zhao, Yun Chai, Shi-Jun Li, Yuanqing Xu, Pan Li
Summary: A visible light-induced kinetic controlled regioselective O-alkylation reaction has been developed for the synthesis of highly stereoselective enol ethers from various 1,3-dicarbonyl compounds using diazoacetates and cyclic ethers under mild and base-free conditions.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Jiupeng Liu, Shuo Tang, Shichong Wang, Mengting Cao, Jingjing Zhao, Puyu Zhang, Pan Li
Summary: A visible-light-induced method for the C-Br bond homolysis of bromomalonates triggered by 1,6-enynes has been developed. This protocol, which is transition-metal-free, photocatalyst-free, and oxidant- and additive-free, offers an efficient approach for divergent synthesis of carbonylated and hydroxylated benzofurans under mild conditions. Mechanistic studies show that the homolysis of C-Br bonds appears to proceed through an energy-transfer pathway, and the atom-transfer radical addition products are crucial intermediates in the generation of carbonylated and hydroxylated benzofurans.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
