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4-Het(aryl)-2-pyrrolidone-3(5)-carboxylic acid alkyl(hetaryl)idenecarbohydrazides: synthesis and structure

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Abstract

4-Het(aryl)-2-pyrrolidone-3(5)-carboxylic acid hydrazides react with aromatic aldehydes, acetone, and acetophenone to give new representatives of N´-alkyl(hetaryl)idenecarbohydrazides of (3R*,4S*)-4-het(aryl)-2-pyrrolidone-3- and (4R*,5R*)-4-het(aryl)-2-pyrrolidone-5-carboxylic acids.

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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, Ratsetams: metody sinteza i biologicheskaya aktivnost´. Monographiya [Racetams: Synthesis and Biological Activity. A 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. Pat. GB 1039113; Chem. Abstrs, 1966, 65, 13672a.

    Google Scholar 

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

    Google Scholar 

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

    Article  CAS  Google Scholar 

  6. Vad. V. Negrebetsky, S. V. Vorobyev, E. P. Kramarova, A. G. Shipov, T. A. Shmigol, Yu. I. Baukov, A. A. Lagunin, A. A. Korlyukov, D. E. Arkhipov, Russ. Chem. Bull., 2018, 67, 1518.

    Article  CAS  Google Scholar 

  7. E. Zeller, H. Stief, B. Pf lug, M. Sastre-y-Hernandez, Pharmacopsychiatry, 1984, 17, 188.

    Article  CAS  Google Scholar 

  8. K. Nakamura, CNS Drug Rev., 2002, 8, 70.

    Article  CAS  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. Kucukguzel, Molecules, 2007, 12, 1910.

    Article  CAS  Google Scholar 

  11. J. Rajput, S. Bagul, S. Ratnamala, R. Bendre, Res. Chem. Intermed., 2017, 43, 6601.

    Article  CAS  Google Scholar 

  12. K. Brokaite, V. Mickevicius, G. Mikulskiene, Chem. Heterocycl. Compd., 2006, 42, 1158.

    Article  CAS  Google Scholar 

  13. K. Anusevicius, J. Jonuskien, B. Sapijanskaite, K. Kantminiene, V. Mickevicius, Res. Chem. Intermed., 2016, 42, 6975.

    Article  CAS  Google Scholar 

  14. 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 

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

    Article  Google Scholar 

  16. Yu. P. Kitaev, Gidrazony [Hydrazones], Nauka, Moscow, 1974, 405 pp. (in Russian).

    Google Scholar 

  17. S. A. Flegontov, Z. S. Titova, B. I. Buzykin, Yu. P. Kitaev, Bull. Acad. Sci. USSR, Div. Chem. Sci., 1976, 25, 541.

    Article  Google Scholar 

  18. N. Demirbas, S. Karaoglu, A. Demirbas, K. Sancak, Eur. J. Med. Chem., 2004, 39, 793.

    Article  CAS  Google Scholar 

  19. V. V. Syakaev, J. Mol. Struct., 2006, 788, 55.

    Article  CAS  Google Scholar 

  20. M. G. Mamolo, V. Falagiani, D. Zampieri, L. Vio, E. Banfi, Il Farmaco, 2001, 56, 587.

    Article  CAS  Google Scholar 

  21. E. Wyrzykiewicz, D. Prukah, J. Heterocycl. Chem., 1998, 35, 381.

    Article  CAS  Google Scholar 

  22. A. Gordon and R. Ford, The Chemist´s Companion, New York, 1972.

  23. G. M. Sheldrick, SADABS, Bruker AXS Inc., Madison (USA), 1997.

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

    Article  Google Scholar 

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

    Article  Google Scholar 

  26. L. J. Farrugia, J. Appl. Crystallogr., 2012, 45, 849.

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Herzen State Pedagogical University of Russia, 48 nab. r. Moiki, 191186, Saint Petersburg, Russian Federation

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

  2. Kazan National Research Technical University named after A. N. Tupolev, 10 ul. K. Marksa, 420111, Kazan, Russian Federation

    F. A. Karamov

  3. Federal Research Center “Kazan Scientific Center of the Russian Academy of Sciences”, A. E. Arbuzov Institute of Organic and Physical Chemistry, 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

Based on the materials of the International Markovnikov Congress on Organic Chemistry (June 21—28, 2019, Moscow—Kazan, Russia).

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 0470—0486, March, 2020.

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Gorodnicheva, N.V., Vasil´eva, O.S., Ostroglyadov, E.S. et al. 4-Het(aryl)-2-pyrrolidone-3(5)-carboxylic acid alkyl(hetaryl)idenecarbohydrazides: synthesis and structure. Russ Chem Bull 69, 470–486 (2020). https://doi.org/10.1007/s11172-020-2786-7

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  • DOI: https://doi.org/10.1007/s11172-020-2786-7

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