- 2,2,2-Trifluoroethoxy Aromatic Heterocycles: Hydrolytically Stable Alternatives to Heteroaryl Chlorides
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Herein we describe the 2,2,2-trifluoroethoxy group as an alternative leaving group for hydrolytically unstable heteroaryl chlorides. This group provides improved shelf stability by years while maintaining reactivity toward nucleophiles in SNAr
- Fisher, Ethan L.,Am Ende, Christopher W.,Humphrey, John M.
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- TYROSINE KINASE NON-RECEPTOR 1 (TNK1) INHIBITORS AND USES THEREOF
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Provided herein is a compound of Formula I: or a pharmaceutically acceptable salt thereof, wherein values for the variables (e.g, X11, X22, R11, R22, R33, R44, R55, R66, R77, R88, m, n) are as described herein. Compounds of Formula I, pharmaceutically acceptable salts thereof, pharmaceutical compositions of either of the foregoing, and combinations of any of the foregoing can be used to treat tyrosine kinase non- receptor 1 (TNK1)-mediated diseases, disorders and conditions.
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Paragraph 00327
(2021/01/23)
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- Room-Temperature Amination of Chloroheteroarenes in Water by a Recyclable Copper(II)-Phosphaadamantanium Sulfonate System
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Buchwald-Hartwig amination of chloroheteroarenes has been a challenging synthetic process, with very few protocols promoting this important transformation at ambient temperature. The current report discusses about an efficient copper-based catalytic system (Cu/PTABS) for the amination of chloroheteroarenes at ambient temperature in water as the sole reaction solvent, a combination that is first to be reported. A wide variety of chloroheteroarenes could be coupled efficiently with primary and secondary amines as well as selected amino acid esters under mild reaction conditions. Catalytic efficiency of the developed protocol also promotes late-stage functionalization of active pharmaceutical ingredients (APIs) such as antibiotics (floxacins) and anticancer drugs. The catalytic system also performs efficiently at a very low concentration of 0.0001 mol % (TON = 980,000) and can be recycled 12 times without any appreciable loss in activity. Theoretical calculations reveal that the π-acceptor ability of the ligand PTABS is the main reason for the appreciably high reactivity of the catalytic system. Preliminary characterization of the catalytic species in the reaction was carried out using UV-VIS and ESR spectroscopy, providing evidence for the Cu(II) oxidation state.
- Dandela, Rambabu,Desai, Aman A.,Kapdi, Anant R.,Kori, Santosh,Maity, Dilip K.,Parmar, Udaysinh,Somvanshi, Dipesh
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p. 8900 - 8925
(2021/07/20)
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- Tert-amino effect-promoted rearrangement of aryl isothiocyanate: A versatile approach to benzimidazothiazepines and benzimidazothioethers
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A general and practical approach to benzimidazothiazepine and benzimidazothioether derivatives via an intramolecular nucleophilic addition/ring expansion rearrangement of aryl isothiocyanates promoted by the tert-amino effect has been developed. This reaction is catalyzed by low-cost camphorsulfonic acid and tolerates a broad substrate scope with complete atom economy. Structurally intriguing benzimidazothiazepine and benzimidazothioether products could be easily obtained by a simple operation in good to excellent yield (up to 98%).
- Geng, Xinyu,Liu, Siyuan,Qu, Jingping,Wang, Baomin,Wang, Wenyao
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p. 12635 - 12643
(2020/11/09)
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- A palladium nanoparticle-catalyzed aryl-amine coupling reaction: High performance of aryl and pyridyl chlorides as the coupling partner
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Carbon nitride (CN)-supported nanosized palladium particles, Pd-CN, have been found to be an active catalyst system for the amination of aryl and pyridyl chloride moieties in the presence of dialkyl amine under mild reaction conditions. The recyclability study of the reaction shows the stable performance of the catalyst without a significant loss of catalytic activity for a couple of cycles.
- Nandi, Debkumar,Islam, Rafique Ul,Devi, Nishu,Siwal, Samarjeet,Mallick, Kaushik
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supporting information
p. 812 - 816
(2018/02/06)
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- Three-component reaction between amines, carbon disulfide and electron-deficient derivatives of chloropyridine or chlorobenzene: Synthesis of 3,6-diazaspiro[4.5]deca-2,7,9-trien-6-ium chloride and dithioylcarbamates derivatives
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In this study, three-component reaction of some primary and secondary amines with carbon disulfide in the presence of electron-deficient derivatives of chloropyridine or chlorobenzene in the CH3CN as a solvent is reported. The reaction of prima
- Ranjbar-Karimi, Reza,Khajeh-Khezri, Aliyeh,Anary-Abbasinejad, Mohammad
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p. 289 - 295
(2014/04/03)
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- Nucleophilic heteroaromatic substitution: Kinetics of the reactions of nitropyridines with aliphatic amines in dipolar aprotic solvents
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Rate data are reported for the reactions of 2-chloro-5-nitropyridine 2a, 2-chloro-3-nitropyridine 2b, and the corresponding 2-phenoxy derivatives 2c with n-butylamine, pyrrolidine and piperidine and 2d with n-butylamine and pyrrolidine in dimethyl sulfoxi
- Isanbor, Chukwuemeka,Emokpae, Thomas A.
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p. 125 - 135
(2008/09/18)
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- The effects of ring substituents and leaving groups on the kinetics of SNAr reactions of 1-halogeno- and 1-phenoxy-nitrobenzenes with aliphatic amines in acetonitrile
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Rate constants are reported for the reactions of a series of 1-chloro-, 1-fluoro- and 1-phenoxy-nitrobenzenes activated by CF3 or CN groups or by ring-nitrogen with n-butylamine, pyrrolidine or piperidine in acetonitrile. The results are compar
- Crampton, Michael R.,Emokpae, Thomas A.,Isanbor, Chukwuemeka
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p. 1378 - 1383
(2008/09/18)
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