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Nitropyrazoles 16. The use of methoxymethyl group as a protecting group for the synthesis of 4-methyl-3-nitro-5-R-pyrazoles

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Abstract

4-Methyl-3,5-dinitropyrazole prepared by nitration of 1,4-dimethylpyrazole readily reacts with methoxymethyl chloride and methyl vinyl ketone in acetonitrile in the presence of a base giving 1-methoxymethyl-4-methyl-3,5-dinitropyrazole and 4-methyl-3,5-dinitro-1-(3-oxobutyl)pyrazole, respectively. The action of the thioglycolanilide anion on 4-methyl-3,5-dinitro-1-(3-oxobutyl)pyrazole results only in the removal of 1-protecting group and the formation of 2-[(3-oxobutyl)thio]acetanilide, while the action of anionic S-nucleophiles on 1-methoxymethyl-4-methyl-3,5-dinitropyrazole leads to the substitution products of the 5-NO2 group in which the methoxymethyl group can be removed by acid hydrolysis.

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Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

    A. A. Zaitsev, I. L. Dalinger, V. V. Kachala, G. P. Popova & S. A. Shevelev

  2. D. I. Mendeleev University of Chemical Technology of Russia, 9 Miusskaya pl., 125047, Moscow, Russian Federation

    I. O. Kortusov

Authors
  1. A. A. Zaitsev
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  2. I. O. Kortusov
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  3. I. L. Dalinger
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  4. V. V. Kachala
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  5. G. P. Popova
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  6. S. A. Shevelev
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Corresponding author

Correspondence to S. A. Shevelev.

Additional information

For Part 15, see Ref. 1.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 10, pp. 2054—2057, October, 2009.

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Zaitsev, A.A., Kortusov, I.O., Dalinger, I.L. et al. Nitropyrazoles 16. The use of methoxymethyl group as a protecting group for the synthesis of 4-methyl-3-nitro-5-R-pyrazoles. Russ Chem Bull 58, 2118–2121 (2009). https://doi.org/10.1007/s11172-009-0289-7

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  • DOI: https://doi.org/10.1007/s11172-009-0289-7

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