- SnCl2/RSH: A versatile catalytic system for the synthesis of 4-Alkylsulfanyl-indazole derivatives
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The treatment of alkylated nitro derivatives of indazole with stannous chloride in alkanethiol gave after coupling of the obtained amines with 4-methoxybenzenesulfonyl chloride in pyridine the new N-(4-Alkylsulfanylindazol-7-yl)-4-methoxybenzene sulfonamides via the nucleophilic substitution of hydrogen in position 4 of indazole, together with the expected 4-methoxy-N-(indazol-7-yl)-benzenesulfonamides. All the newly synthesized compounds have been characterized by elemental analysis and spectroscopic data.
- Kouakou, Assoman,Chicha, Hakima,Rakib, El Mostapha,Gamouh, Ahmed,Hannioui, Abdellah,Chigr, Mohammed,Viale, Maurizio
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- Efficient and regioselective synthesis of 2-alkyl-2H-indazoles
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An efficient and regioselective synthesis of 2-methyl-2H-indazoles and 2-ethyl-2H-indazoles using trimethyloxonium tetrafluoroborate or triethyloxonium hexafluorophosphate is reported.
- Cheung, Mui,Boloor, Amogh,Stafford, Jeffrey A.
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- New nitroindazolylacetonitriles: Efficient synthetic access: Via vicarious nucleophilic substitution and tautomeric switching mediated by anions
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New N-Alkyl-nitroindazolylacetonitriles were efficiently obtained via vicarious nucleophilic substitution of N-methyl-nitroindazoles with 4-chlorophenoxyacetonitrile. All compounds were fully characterized by NMR and mass spectroscopy techniques and the structures of some of them were additionally confirmed by X-ray diffraction analysis data. Tautomeric switching was observed in this series of nitroindazolylacetonitriles upon addition of basic anions followed by UV-Vis spectrophotometric and 1H-NMR titrations. The formation of tautomeric species induced by anionic species was endorsed by Density Functional Theory calculations.
- Eddahmi, Mohammed,Moura, Nuno M. M.,Bouissane, Latifa,Gamouh, Ahmed,Faustino, Maria A. F.,Cavaleiro, José A. S.,Paz, Filipe A. A.,Mendes, Ricardo F.,Lodeiro, Carlos,Santos, Sérgio M.,Neves, Maria G. P. M. S.,Rakib, El Mostapha
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p. 14355 - 14367
(2019/09/30)
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- Regioselective methylation of indazoles using methyl 2,2,2- trichloromethylacetimidate
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An efficient and regio selective synthesis of substituted 2-methyl-2H-indazoles using a methyl 2,2,2-trichloroacetimidate is described.
- Baddam, Sudhakar Reddy,Uday Kumar,Panasa Reddy,Bandichhor, Rakeshwar
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supporting information
p. 1661 - 1663
(2013/03/29)
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- Fluorinated indazoles as novel selective inhibitors of nitric oxide synthase (NOS): Synthesis and biological evaluation
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In order to find new compounds with neuroprotective activity and NOS-I/NOS-II selectivity, we have designed, synthesized, and characterized 14 new NOS inhibitors with an indazole structure. The first group corresponds to 4,5,6,7-tetrahydroindazoles (4-8), the second to the N-methyl derivatives (9-12) of 7-nitro-1H-indazole (1) and 3-bromo-7-nitro-1H-indazole (2), and the latter to 4,5,6,7-tetrafluoroindazoles (13-17). Compound 13 (4,5,6,7-tetrafluoro-3-methyl-1H-indazole) inhibited NOS-I by 63% and NOS-II by 83%. Interestingly, compound 16 (4,5,6,7-tetrafluoro-3-perfluorophenyl-1H-indazole) inhibited NOS-II activity by 80%, but it did not affect to NOS-I activity. Structural comparison between these new indazoles further supports the importance of the aromatic indazole skeleton for NOS inhibition and indicate that bulky groups or N-methylation of 1 and 2 diminish their effect on NOS activity. The fluorination of the aromatic ring increased the inhibitory potency and NOS-II selectivity, suggesting that this is a promising strategy for NOS selective inhibitors.
- Claramunt, Rosa M.,Lopez, Concepcion,Perez-Medina, Carlos,Perez-Torralba, Marta,Elguero, Jose,Escames, Germaine,Acuna-Castroviejo, Dario
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experimental part
p. 6180 - 6187
(2011/02/26)
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- Reduction of nitroindazoles: Preparation of new amino and chloroamino derivatives
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The synthesis of chloroaminoindazoles by the reduction of the nitro group of indazoles using stannous chloride in alcoholic acid solution is reported. Using catalytic hydrogenation with palladium the expected reduction to amino-indazoles occur.{A figure is presented}. Indazole Nitro Reduction Chlorination Aminochloroindazole Heterocycle.
- Miloudi, Abdellah,El Abed, Douniazed,Boyer, Gerard,Galy, Jean-Pierre
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p. 2595 - 2605
(2008/02/04)
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