Chemistry of Heterocyclic Compounds

, Volume 52, Issue 8, pp 574–577 | Cite as

3-(Nitromethyl)-3,4-dihydroquinoxalin-2(1H)-ones: synthesis and structure

  • Vasilii V. Pelipko
  • Sergey V. Makarenko
  • Valentina M. BerestovitskayaEmail author
  • Ruslan I. Baichurin

Reactions of ethyl 3-nitroacrylate with o-phenylenediamine and its substituted derivatives were used for the synthesis of 3-(nitromethyl)-3,4-dihydroquinoxalin-2(1H)-ones, followed by structural characterization. These compounds were found to undergo elimination of nitromethane, leading to quinoxalin-2(1H)-ones.


1,2-diaminobenzene ethyl 3-nitroacrylate 3-(nitromethyl)-3,4-dihydroquinoxalin-2(1H)-one quinoxalin-2(1H)-one aza-Michael reaction 


This work received financial support from the Ministry of Education and Science of Russian Federation, within the framework of baseline of the State Assignment.

Supplementary material

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  1. 1.
    Pereira, J. A.; Pessoa, A. M.; Cordeiro, M. N. D. S.; Fernandes, R.; Prudêncio, C.; Noronha, J. P.; Vieira, M. Eur. J. Med. Chem. 2015, 97, 664.CrossRefGoogle Scholar
  2. 2.
    General Organic Chemistry [Russian translation]; Barton, D.; Ollis, W. D., Eds.; Khimiya: Moscow, 1985, Vol. 8, p. 161.Google Scholar
  3. 3.
    Waring, M. J.; Wakelin, L. P. G. Nature 1974, 252, 653.CrossRefGoogle Scholar
  4. 4.
    Kim, Y. B.; Kim, Y. H.; Park, J. Y.; Kim, S. K. Bioorg. Med. Chem. Lett. 2004, 14, 541.CrossRefGoogle Scholar
  5. 5.
    Mashkovsky, M. D. Drugs [in Russian]; Novaya Volna: Moscow, 2002, 14th ed., Vol. 2, p. 298.Google Scholar
  6. 6.
    Russian Drug Directory. Encyclopedia of Medicines [in Russian]; RLS, Moscow, 2002, 2nd ed., p. 305, 938.Google Scholar
  7. 7.
    Carta, A.; Piras, S.; Loriga, G.; Paglietti, G. Mini-Rev. Med. Chem. 2006, 6, 1179.CrossRefGoogle Scholar
  8. 8.
    El-Sabbagh, O. I.; El-Sadek, M. E.; Lashine, S. M.; Yassin, S. H.; El-Nabtity, S. M. Med. Chem. Res. 2009, 18, 782.CrossRefGoogle Scholar
  9. 9.
    Ajani, O. O.; Obafemi, C. A.; Ikpo, C. O.; Ogunniran, K. O.; Nwinyi, O. C. Chem. Heterocycl. Compd. 2009, 45, 1370. [Khim. Geterotsikl. Soedin. 2009, 1703.]Google Scholar
  10. 10.
    Gupta, D.; Ghosh, N. N.; Chandra, R. Bioorg. Med. Chem. Lett. 2005, 15, 1019.CrossRefGoogle Scholar
  11. 11.
    Rösner, M.; Billhardt-Troughton, U.-M.; Kirsh, R.; Kleim, J.-P.; Meichsner, C.; Riess, G.; Winkler, I. US Patent 5723461.Google Scholar
  12. 12.
    Sarges, R.; Lyga, J. W. J. Heterocycl. Chem. 1988, 25, 1475.CrossRefGoogle Scholar
  13. 13.
    Lee, L.; Murray, W. V.; Rivero, R. A. J. Org. Chem. 1997, 62, 3874.CrossRefGoogle Scholar
  14. 14.
    Suschitzky, H.; Wakefield, B. J.; Whittaker, R. A. J. Chem. Soc., Perkin Trans. 1 1975, 401.Google Scholar
  15. 15.
    Kim, Y.; Lee, M. H.; Choi, E. T.; No, E. S.; Park, Y. S. Heterocycles 2007, 71, 5.CrossRefGoogle Scholar
  16. 16.
    Chupakhin, O. N.; Egorov, I. N.; Rusinov, V. L.; Slepukhin, P. A. Russ. Chem. Bull. 2010, 59, 991. [Izv. Akad. Nauk, Ser. Khim. 2010, 970.]Google Scholar
  17. 17.
    Carrër, A.; Brion, J.-D.; Messaoudi, S.; Alami, M. Org. Lett. 2013, 15, 5606.CrossRefGoogle Scholar
  18. 18.
    Murata, S.; Sugimoto, T.; Matsuura, S. Heterocycles 1987, 26, 883.CrossRefGoogle Scholar
  19. 19.
    Ballini, R.; Gabrielli, S.; Palmieri, A. Synlett 2009, 965.Google Scholar
  20. 20.
    Kazimierczuk, Z.; Pfleiderer, W. Liebigs Ann. Chem. 1982, 754.Google Scholar
  21. 21.
    Silverstein, R.; Webster, F.; Kimle, D. Spectrometric Identification of Organic Compounds [Russian translation]; BINOM. Laboratoriya Znanii: Moscow, 2012, p. 557.Google Scholar
  22. 22.
    Pretsch, E.; Buhlmann, P.; Affolter, C. Structure Determination of Organic Compounds. Tables of Spectral Data [Russian translation]; Mir; BINOM. Laboratoriya Znanii: Moscow, 2006.Google Scholar
  23. 23.
    Dawson, W.; Newbold, G. T.; Spring F. S. J. Chem. Soc. 1949, 2579.Google Scholar
  24. 24.
    Pflegel, P.; Wagner, G. Z. Chem. (Stuttgart, Ger.) 1968, 8, 179.Google Scholar
  25. 25.
    Marxer, A.; Salzmann, U.; Hofer F. Helv. Chim. Acta 1971, 54, 2507.CrossRefGoogle Scholar
  26. 26.
    McMurry, J. E.; Musser, J. H.; Fleming, I.; Fortunak, J.; Nübling, C. Org. Synth. 1977, 56, 65.CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 2016

Authors and Affiliations

  • Vasilii V. Pelipko
    • 1
  • Sergey V. Makarenko
    • 1
  • Valentina M. Berestovitskaya
    • 1
    Email author
  • Ruslan I. Baichurin
    • 1
  1. 1.Herzen State Pedagogical University of RussiaSaint PetersburgRussia

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