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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 49, 2019 - Issue 5
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Articles

Oxidation of 1,4-disubstituted-1,2,3-triazoles with H2O2-CF3CO2H: efficient synthesis of 1,2,3-triazole 3-oxides

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Pages 679-687 | Received 10 Aug 2018, Accepted 03 Jan 2019, Published online: 06 Feb 2019

References

  • Zhu, J.; Kong, Y.; Lin, F.; Wang, B.; Chen, Z.; Liu, L. Copper-Catalyzed Direct Amination of 1,2,3-Triazole N -Oxides by C-H Activation and C-N Coupling. Eur. J. Org. Chem. 2015, 2015, 1507-1515. DOI: 10.1002/ejoc.201403583.
  • Zhu, J.; Chen, Y.; Lin, F.; Wang, W.; Huang, Q.; Liu, L. Synlett 2015, 26, 1124-1130.
  • Liu, W.; Li, Y.; Wang, Y.; Kuang, C. Site-Selective Direct Arylation of 1,2,3-Triazole N -Oxides. Eur. J. Org. Chem. 2013, 2013, 5272-5275. DOI: 10.1002/ejoc.201300747
  • Tian, Q.; Chen, X.; Liu, W.; Wang, Z.; Shi, S.; Kuang, C. Regioselective Halogenation of 2-substituted-1,2,3-triazoles via sp2 C-H Activation. Org. Biomol. Chem. 2013, 11, 7830-7833. DOI: 10.1039/c3ob41558a
  • Mitchell, W. R.; Paton, R. M. ARKIVOC 2010, 2010, 34-54.
  • Butler, R. N.; Cunningham, D.; Marren, E. G.; McArdle, P. Extended Tandem Reactions of 2H-1,2,3-triazole N-oxides with Dialkyl Acetylenedicarboxylates and N-phenylmaleimide: substituted Monocyclic 2,5-dihydro-1,2,3-triazines and New Tetrahydrofuro[2,3-d]-1,2,3-triazoles. Azolium 1,3-dipoles Part 5. J. Chem. Soc, Perkin Trans. 1 1990, 1990, 3321-3326.
  • Peng, X.; Huang, H.; Jiang, L.; Zhu, J.; Liu, L. Palladium-catalyzed Highly Regioselective Oxidative Homocoupling of 1,2,3-triazole N-Oxides. Tetrahedron Lett. 2016, 57, 5223-5226. DOI: 10.1016/j.tetlet.2016.10.032
  • Amitina, S. A.; Volodarskii, L. B. Conversion of ?-Azoxyoximes to 2H-1,2,3-triazole N-oxide Derivatives. Chem. Heterocycl. Compd. 1973, 9, 120-122. DOI: 10.1007/BF00476168
  • Godovikova, T. I.; Ignat'eva, E. L.; Khmel'nitskii, L. I. Synthesis and Properties of 1,2,3-triazole 1-oxides (review). Chem. Heterocycl. Compd. 1989, 25, 113-121. DOI: 10.1007/BF00479900
  • Theocharis, A. B.; Maroulis, A. J.; Hadjiantoniou-Maroulis, C. P.; Alexandrou, N. E. Synthesis, Structure, and Acylating Properties of 1-aroyloxy-4,5-dimethyl-1,2,3-Triazoles. J. Chem. Soc. Perk. T. 1 1989, 1989, 619-621.
  • Jiang, L.; Davison, A.; Tennant, G.; Ramage, R. Synthesis and Application of a Novel Coupling Reagent, ethyl 1-hydroxy-1H -1,2,3-triazole-4-Carboxylate. Tetrahedron 1998, 54, 14233-14254. DOI: 10.1016/S0040-4020(98)00876-X
  • Stensbøl, T. B.; Uhlmann, P.; Morel, S.; Eriksen, B. L.; Felding, J.; Kromann, H.; Hermit, M. B.; Greenwood, J. R.; Brauner-Osborne, H.; Madsen, U.; et al. Novel 1-Hydroxyazole Bioisosteres of Glutamic Acid. Synthesis, Protolytic Properties, and Pharmacology. J. Med. Chem. 2002, 45, 19-31. DOI: 10.1021/jm010303j
  • Begtrup, M.; Nytoft, H. P. Acta Chem. Scand. B. 1986, 40, 262-269.
  • Begtrup, M.; Vedsø, P.; Hegbom, I.; Ranes, E.; Nielsen, B.; Nielsen, R. I.; Olsen, C. E.; Rosendahl, C. N.; Haugg, M.; Trabesinger-Rüf, N.; Weinhold, E. G. Preparation of 1-Hydroxypyrazoles and 1-Hydroxy-1,2,3-triazoles by Dealkylation of Pyrazole and Triazole N-Oxides. Acta Chem. Scand. 1996, 50, 549-555. DOI: 10.3891/acta.chem.scand.50-0549
  • Apasov, E. T.; Churakov, A. M.; Strelenko, Y. A.; Ioffe, S. L.; Djetigenov, B. A.; Tartakovsky, V. A. A Synthesis of 1-hydroxybenzo-1,2,3-triazole 3-Oxide. Tetrahedron 1995, 51, 6775-6782. DOI: 10.1016/0040-4020(95)00310-5
  • Begtrup, M.; Jonsson, G. Acta Chem. Scand. B 1987, 41, 724-735.
  • Youssif, S. ARKIVOC 2001, 2001, 242-268.
  • Tornoe, C. W.; Christensen, C.; Meldal, M. Peptidotriazoles on Solid Phase: [1,2,3]-Triazoles by Regiospecific Copper(i)-Catalyzed 1,3-dipolar Cycloadditions of Terminal Alkynes to Azides. J. Org. Chem. 2002, 67, 3057-3064. DOI: 10.1021/jo011148j
  • Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. A Stepwise Huisgen Cycloaddition Process: Copper(I)-Catalyzed Regioselective &quot;ligation&quot; of Azides and Terminal Alkynes. Angew. Chem. Int. Ed. Engl. 2002, 41, 2596-2599. DOI: 10.1002/1521-3773(20020715)41:14<2596::AID-ANIE2596>3.0.CO;2-4
  • Meldal, M.; Tornoe, C. W. Cu-Catalyzed Azide-Alkyne Cycloaddition. Chem. Rev. 2008, 108, 2952-3015. DOI: 10.1021/cr0783479
  • Moses, M. E.; Moorhouse, A. D. The Growing Applications of Click Chemistry. Chem. Soc. Rev. 2007, 36, 1249-1262. DOI: 10.1039/B613014N.
  • Bock, V. D.; Hiemstra, H.; van Maarseveen, J. H. CuI-Catalyzed Alkyne-Azide “Click” Cycloadditions from a Mechanistic and Synthetic Perspective. Eur. J. Org. Chem. 2006, 2006, 51-68. DOI: 10.1002/ejoc.200500483
  • Ochiai, E. Recent Japanese Work on the Chemistry of Pyridine 1-OXIDE and Related Compounds. J. Org. Chem. 1953, 18, 534-551. DOI: 10.1021/jo01133a010
  • Boekelheidaen, V.; Linn, W. J. J. Am. Chem. Soc. 1954, 76, 1286-1291. DOI: 10.1021/ja01634a026
  • Caron, S.; Do, N. M.; Sieser, J. E. A Practical, Efficient, and Rapid Method for the Oxidation of Electron Deficient Pyridines Using Trifluoroacetic Anhydride and Hydrogen Peroxide-Urea Complex. Tetrahedron Lett. 2000, 41, 2299-2302. DOI: 10.1016/S0040-4039(00)00165-9
  • Zhao, X.; Zhang, T.; Zhou, Y.; Liu, D. Preparation of Peracetic Acid from Hydrogen Peroxide. J. Mol. Catal. A. 2007, 271, 246-252. DOI: 10.1016/j.molcata.2007.03.012
  • Hiyama, T. Trifluoroacetic Acid and Trifluoroperacetic Acid. In Organofluorine Compounds: Chemistry and Applications; Springer Verlag: Berlin, 2000; pp. 255-257.
  • Velasco, B. E.; López-Téllez, G.; González-Rivas, N.; García-Orozco, I.; Cuevas-Yañez, E. Catalytic Activity of Dithioic Acid Copper Complexes in the Alkyne-azide Cycloaddition. Can. J. Chem. 2013, 91, 292-299. DOI: 10.1139/cjc-2012-0325.
  • Velasco, B. E.; Fuentes, A.; Gonzalez, C.; Corona, D.; García-Orozco, I.; Cuevas Yañez, E. Synthesis of (Tetrahydrofuranyl)methyl-1,2,3-triazoles through Alkyne-Azide Cycloaddition Catalyzed by a Dithioic Acid Copper(I) Complex. Synth. Commun. 2011, 41, 2966-2973. DOI: 10.1080/00397911.2010.516052
  • Mereyala, H. B.; Gurrala, S. G.; Mohan, S. K. Study of Metal and Acid Catalysed Deprotection of Propargyl Ethers of Alcohols via Their Allenyl Ethers. Tetrahedron 1999, 55, 11331-11342. DOI: 10.1016/S0040-4020(99)00631-6
  • Snyder, C. D.; Rapoport, H. Oxidative Cleavage of Hydroquinone Ethers with Argentic Oxide. J. Am. Chem. Soc. 1972, 94, 227-231. DOI: 10.1021/ja00756a040
  • Ueno, S.; Mizushima, E.; Chatani, N.; Kakiuchi, F. Direct Observation of the Oxidative Addition of the Aryl Carbon-oxygen Bond to a Ruthenium Complex and Consideration of the Relative Reactivity between Aryl Carbon-Oxygen and Aryl Carbon-Hydrogen Bonds. J. Am. Chem. Soc. 2006, 128, 16516-16517. DOI: 10.1021/ja067612p
  • Ozanne, A.; Pouységu, L.; Depernet, D.; François, B.; Quideau, S. A Stabilized Formulation of IBX (SIBX) for Safe Oxidation Reactions Including a New Oxidative Demethylation of Phenolic Methyl Aryl Ethers. Org. Lett. 2003, 5, 2903-2906. DOI: 10.1021/ol0349965

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