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2-[4-(Het)aryl-2-oxopyrrolidin-1-yl]acetohydrazides: synthesis, structures, and reactions with carbonyl compounds

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Abstract

2-[4-(Het)aryl-2-oxopyrrolidin-1-yl]acetohydrazides, structural analogs of piracetam, were synthesized by the condensation of 2-[4-(het)aryl-2-oxopyrrolidin-1-yl]acetates with hydrazine hydrate and phenylhydrazine. New [N′-alkyl(hetaryl)idene]-4-(het)aryl-2-oxopyrrolidin-1-ylacetohydrazides were synthesized by the reaction of 2-[4-(het)aryl-2-oxopyrrolidin-1-yl]-acetohydrazides with aromatic aldehydes, acetone, and acetophenone.

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References

  1. V. M. Berestovitskaya, I. N. Tyurenkov, O. S. Vasil'eva, V. N. Perfilova, E. S. Ostroglyadov, V. V. Bagmetova, Ratsetamy: metody sinteza i biologicheskaya aktivnost'. Monografiya [Racetams: Methods of Synthesis and Biological Activity. Monograph], Asterion, St. Petersburg, 2016, 287 pp. (in Russian).

    Google Scholar 

  2. M. D. Mashkovskii, Lekarstvennye sredstva [Drugs], 16th ed., Novaya Volna, Moscow, 2012, 1216 pp. (in Russian).

    Google Scholar 

  3. GB Pat. 1039113; Chem. Abstrs., 1966, 65, 13672a.

    Google Scholar 

  4. V. G. Granik, Lekarstva (farmakologicheskii, biokhimicheskii i khimicheskii aspekty) [Drugs, (Pharmacological, Biochemical, and Chemical Aspects)], 2nd ed., Vuzovskaya kniga, Moscow, 2006, pp. 149, 153, 360 (in Russian).

    Google Scholar 

  5. A. Malykh, M. Sadaie, Drugs, 2010, 70, 287.

    Article  CAS  Google Scholar 

  6. A. Gouliaev, J. Monster, M. Vedso, A. Senning, Org. Prep. Proced. Int., 1995, 27, 273.

    Article  CAS  Google Scholar 

  7. US Pat. 4696943 A1; Chem. Abstrs., 1986, 105, 018467.

    Google Scholar 

  8. RF Pat. 2440981; Chem. Abstrs., 2012, 156, 230440.

    Google Scholar 

  9. D. Rando, D. Sato, L. Siqueira, A. Malvezzi, C. Leite, A. Amaral, F. Ferreira, L. Tavares, Bioorg. Med. Chem., 2002, 10, 557.

    Article  CAS  Google Scholar 

  10. S. Rollas, G. Küçükgüzel, Molecules, 2007, 12, 1910.

    Article  CAS  Google Scholar 

  11. O. M. Glozman, I. S. Morozov, L. A. Zhmurenko, V. A. Zago revskii, Pharm. Chem. J., 1980, 14, 776.

    Article  Google Scholar 

  12. M. Kenda, A. Matagne, P. Talaga, P. Pasau, E. Diferding, B. Lallemand, A. Frycia, F. Moureau, H. Klitgaard, M. Gil-lard, B. Fuks, P. Michel, J. Med. Chem., 2004, 47, 530.

    Article  CAS  Google Scholar 

  13. GB Pat. 0004297, 2000.

  14. R. Ya. Popova, T. A. Gudasheva, S. S. Trofimov, R. U. Ostrovskaya, A. P. Skoldinov, Pharm. Chem. J., 1983, 17, 858.

    Article  Google Scholar 

  15. N. V. Gorodnicheva, E. S. Ostroglyadov, O. S. Vasil'eva, V. V. Pelipko, V. V. Gurzhii, V. M. Berestovitskaya, E. S. Lipina, Russ. J. Org. Chem., 2016, 52, 1616.

    Article  CAS  Google Scholar 

  16. O. S. Vasil'eva, B. M. Berestovitskaya, I. N. Tyurenkov, E. S. Ostroglyadov, V. N. Perfilova, N. V. Gorodnicheva, A. I. Yaremchuk, Russ. Chem. Bull., 2017, 66, 1491.

    Article  CAS  Google Scholar 

  17. O. S. Vasil'eva, E. S. Ostroglyadov, N. V. Gorodnicheva, S. V. Makarenko, I. N. Tyurenkov, V. N. Perfilova, S. M. Aleksandrova, Russ. J. Gen. Chem., 2018, 88, 1374.

    Article  CAS  Google Scholar 

  18. K. Brokaite, V. Mickevicius, G. Mikulskiene, Chem. Hetero-cycl. Compd., 2006, 42, 1158.

    Article  CAS  Google Scholar 

  19. K. Anusevicius, J. Jonuskiene, B. Sapijanskaite, K. Kantmini-ene, V. Mickevicius, Res. Chem. Intermed., 2016, 42, 6975.

    Article  CAS  Google Scholar 

  20. G. M. Sheldrick, SADABS. Bruker AXS Inc., Madison, USA, 1997.

  21. G. M. Sheldrick, Acta Crystallogr., Sect. A: Found. Adv., 2015, 71, 3.

    Article  Google Scholar 

  22. G. M. Sheldrick, Acta Crystallogr., Sect. C: Struct. Chem., 2015, 71, 3.

    Article  Google Scholar 

  23. L. J. Farrugia, J. Appl. Cryst., 2012, 45, 849.

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Herzen State Pedagogical University of Russia, 48 nab. Moika, 191186, St. Petersburg, Russian Federation

    N. V. Gorodnicheva, O. S. Vasil’eva, E. S. Ostroglyadov, R. I. Baichurin & S. V. Makarenko

  2. Kazan National Research Technological University named after A. N. Tupolev (KAI), 10 ul. K Marksa, 420111, Kazan, Russian Federation

    F. A. Karamov & I. A. Litvinov

  3. A. E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center of the Russian Academy of Sciences, 8 ul. Akad. Arbuzova, 420088, Kazan, Russian Federation

    O. A. Lodochnikova & I. A. Litvinov

Authors
  1. N. V. Gorodnicheva
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  2. O. S. Vasil’eva
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  3. E. S. Ostroglyadov
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  4. R. I. Baichurin
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  5. S. V. Makarenko
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  6. F. A. Karamov
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  7. O. A. Lodochnikova
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  8. I. A. Litvinov
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Corresponding author

Correspondence to S. V. Makarenko.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 5, pp. 0996–1008, May, 2020.

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Gorodnicheva, N.V., Vasil’eva, O.S., Ostroglyadov, E.S. et al. 2-[4-(Het)aryl-2-oxopyrrolidin-1-yl]acetohydrazides: synthesis, structures, and reactions with carbonyl compounds. Russ Chem Bull 69, 996–1008 (2020). https://doi.org/10.1007/s11172-020-2861-0

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  • DOI: https://doi.org/10.1007/s11172-020-2861-0

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