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Synthesis and transformations of perfluoroalkyl-containing 6,7-dihydro-1H-indazol-4(5H)-ones oximes

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Abstract

Refluxing 3-perfluoroalkyl-6,7-dihydro-1H-indazol-4(5H)-ones with 4-fold excess of hydroxylamine hydrochloride in pyridine afforded their (E)-oximes. The obtained oximes were alkylated with ethyl iodide and acylated with carboxylic acids chlorides to obtain (E)-O-alkyl- and (E)-O-acyloximes respectively. Heating oximes in PPA at 120°C results in their aromatization by Semmler-Wolff reaction, hydrolysis of perfluoroalkyl groups, and generation of 4-amino-1-aryl-5,6-dimethyl-1H-indazole-3-carboxylic acids from of 3-tri-fluoromethylindazolone oximes and 1-(4-amino-1-aryl-5,6-dimethyl-1H-indazol-3-yl)-fluoroalkan-1-ones from of 3-perfluoroethyl- and 3-perfluoropropylindazolone oximes.

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Authors and Affiliations

  1. Institute of Bioorganic Chemistry, National Academy of Sciences of Belarus, ul. Akademika Kuprevicha 5/2, Minsk, 220141, Belarus

    T. S. Khlebnikova, Yu. A. Piven’, A. V. Baranovskii & F. A. Lakhvich

Authors
  1. T. S. Khlebnikova
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  2. Yu. A. Piven’
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  3. A. V. Baranovskii
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  4. F. A. Lakhvich
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Correspondence to T. S. Khlebnikova.

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Original Russian Text © T.S. Khlebnikova, Yu.A. Piven’, A.V. Baranovskii, F.A. Lakhvich, 2015, published in Zhurnal Organicheskoi Khimii, 2015, Vol. 51, No. 5, pp. 669–675.

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Khlebnikova, T.S., Piven’, Y.A., Baranovskii, A.V. et al. Synthesis and transformations of perfluoroalkyl-containing 6,7-dihydro-1H-indazol-4(5H)-ones oximes. Russ J Org Chem 51, 650–656 (2015). https://doi.org/10.1134/S1070428015050115

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  • DOI: https://doi.org/10.1134/S1070428015050115

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