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β-Acetyl-β-nitrostyrenes: Structure and use for synthesis of heteryl-containing structures

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Abstract

1H, IR, and electronic absorption spectroscopy and X-ray diffraction analysis were used to establish that 1-acetyl-1-nitro-2-phenyl-and 2-(p-methoxyphenyl)ethenes have Z configuration, and their 2-(p-N,Ndimethylaminophenyl)-substituted analog exists in chloroform-d 3 as a mixture of Z and E isomers. The reactions of gem-acetylnitroethenes with N-methylpyrrole were shown to involve alkylation at the C2-reaction center of the heterocycle. The reactions of these nitroalkenes with hydrazine form pyrazoles and azines, with acetylhydrazine, the corresponding hydrazones (via transalkenylation), and with sodium azide, acetylsubstituted 1,2,3-triazoles.

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References

  1. Fel’gendler, A.V., Aboskalova, N.I., and Berestovitskaya, V.M., Zh. Obshch. Khim., 2000, vol. 70, no. 7, p. 1158.

    Google Scholar 

  2. Aboskalova, N.I., Fel’gendler, A.V., Sheremet, E.A., Trukhin, E.V., and Berestovitskaya, V.M., Zh. Org. Khim., 2003, vol. 39, no. 5, p. 790.

    Google Scholar 

  3. Aboskalova, N.I., Berestovitskaya, V.M., Berkova, G.A., and Fel’gendler, A.V., Zh. Org. Khim., 1999, vol. 35, no. 1, p. 156.

    Google Scholar 

  4. Remennikov, G.Ya., Shavran, S.S., Boldyrev, I.V., Kurilenko, L.K., Klebanov, B.M., and Kukhar’, V.G., Khim.-Pharm. Zh., 1991, vol. 25, no. 3, p. 35.

    CAS  Google Scholar 

  5. Remennikov, G.Ya., Boldyrev, I.V., Kapran, N.A., and Kurilenko, L.K., Khim. Geterotsikl. Soedin., 1993, no. 3, p. 388.

  6. Remennikov, G.Ya., Boldyrev, I.V., Kravchenko, S.A., and Pirozhenko, V.V., Khim. Geterotsikl. Soedin., 1993, no. 9, p. 1290.

  7. Remennikov, G.Ya., Boldyrev, I.V., Kravchenko, S.A., and Pirozhenko, V.V., Khim. Geterotsikl. Soedin., 1993, no. 10, p. 1398.

  8. Trukhin, E.V., Makarenko, S.V., and Berestovitskaya, V.M., Zh. Org. Khim., 1998, vol. 34. no. 1, p. 72.

    Google Scholar 

  9. Peprno, T.Ya., Perekalin, V.V., and Sopova, A.S., Zh. Prikl. Spektrosk., 1973, vol. 19, no. 4, p. 649.

    Google Scholar 

  10. Peprno, T.Ya. and Perekalin, V.V., Infrakrasnye spektry nitrosoyedinenii (Infrared Spectra of Nitro Compounds), Leningrad: Len. Gos. Ped. Inst. im. A.I. Gertsena, 1974, p. 185.

    Google Scholar 

  11. Wallis, J.D., and Watkin, D.J., Acta Crystallogr., Sect. B, 1982, vol. 38, part 7, p. 2057.

    Article  Google Scholar 

  12. Panfilova, L.V., Antipin, M.Yu., Churkin, Yu.D., and Struchkov, Yu.T., Khim. Geterotsikl. Soedin., 1979, no. 9, p. 1201.

  13. Yuryev, Yu.K., Zefirov, N.S., and Shteinman, A.A., Zh. Obshch. Khim., 1963, vol. 33, no. 4, p. 1150.

    Google Scholar 

  14. Cambell, M.M., Cosford, N. Zongli li, and Sainsbury, M., Tetrahedron, 1987, vol. 43, no. 6, p. 1117.

    Article  Google Scholar 

  15. Lin, C., Hsu, J., Sastry, M.N.V., Fang, H., Tu, Z., Liu, J., and Ching-Fa, Y., Tetrahedron, 2005, vol. 61, no. 49, p. 11751.

    Article  CAS  Google Scholar 

  16. Nenaydenko, V.G., Sanin, A.V., and Balenkova, E.S., Zh. Org. Khim., 1995, vol. 31, no. 5, p. 786.

    Google Scholar 

  17. Long, L.M. and Troutman, H.D., J. Am. Chem. Soc., 1949, vol. 71, no. 7, p. 2469.

    Article  CAS  Google Scholar 

  18. El-Rayyes, N.R., Novakeemian, G.H., and Hammoud, H.S., J. Chem. Eng. Data, 1984, vol. 29, no. 2, p. 225.

    Article  CAS  Google Scholar 

  19. Mathieu, J. and Panico, R., Mécanismes Réactionnels en Chimie, Paris: Hermann, 1972. Translated under the title Printsypy organicheskogo sinteza, Leningrad: Khimiya, 1962, p. 591.

    Google Scholar 

  20. Aboskalova, N.I., Berestovitskaya, V.M., Bakhareva, S.V., and Fel’gendler, A.V., Khim. Geterotsikl. Soedin., 2002, no. 10, p. 1462.

  21. Moureu C. and Brachin M., C. r. Acad. Chem. Fr., 1903, vol. 136, p. 1262.

    CAS  Google Scholar 

  22. Sjollema B., Justus Liebigs Ann. Chem., 1894, vol. 279, p. 248.

    Article  Google Scholar 

  23. Liadergen, C.R. and Niemann, C., J. Am. Chem. Soc., 1949, vol. 71, no. 4, p. 1504.

    Google Scholar 

  24. Zefirov, N.S., Chapovskaya, N.K., and Kolesnikov, V.V., Chem. Commun., 1971, no. 17, p. 1001.

  25. Khusamutdinov, G.Kh., Bondarenko, O.A., Kupriyanova, L.A., Klimenko, V.G., and Demina, L.A., Zh. Org. Khim., 1979, V. 15, no. 6, p. 1307.

    Google Scholar 

  26. Khusamutdinov, G.Kh., Bondarenko, O.A., and Kupriyanova, L.A., Zh. Org. Khim., 1975, vol. 11, no. 11, p. 2445.

    Google Scholar 

  27. Sheremet, E.A., Tomanov, R.I., Trukhin, E.V., and Berestovitskaya, V.M., Zh. Org. Khim., 2004, vol. 40, no. 4, p. 620.

    Google Scholar 

  28. Bakhareva, S.V., Aboskalova, N.I., and Berestovitskaya, V.M., Zh. Obshch. Khim., 2001, vol. 71, no. 9, p. 1577.

    Google Scholar 

  29. Beck, G. and Günther, D.,, Chem. Ber., 1973, vol. 106, no. 9, p. 2758.

    Article  CAS  Google Scholar 

  30. Beilst, H.: a) 23, 186; b) 14, 36.

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Authors and Affiliations

  1. Gertsen Russian State Pedagogical University, nab. r. Moiki 48, St. Petersburg, 191186, Russia

    N. I. Aboskalova, N. N. Smirnova, R. I. Baichurin, A. V. Fel’gendler, G. A. Berkova & V. M. Berestovitskaya

  2. Arbuzov Institute of Organic and Physical Chemistry, Kazan Research Center, Russian Academy of Sciences, Kazan, Tatarstan, Russia

    O. N. Kataeva

Authors
  1. N. I. Aboskalova
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  2. N. N. Smirnova
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  3. O. N. Kataeva
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  4. R. I. Baichurin
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  5. A. V. Fel’gendler
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  6. G. A. Berkova
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  7. V. M. Berestovitskaya
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Correspondence to N. I. Aboskalova.

Additional information

Original Russian Text © N.I. Aboskalova, N.N. Smirnova, O.N. Kataeva, R.I. Baichurin, A. V. Fel’gendler, G.A. Berkova, V.M. Berestovitskaya, 2008, published in Zhurnal Obshchei Khimii, 2008, Vol. 78, No. 9, pp. 1479–1488.

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Aboskalova, N.I., Smirnova, N.N., Kataeva, O.N. et al. β-Acetyl-β-nitrostyrenes: Structure and use for synthesis of heteryl-containing structures. Russ J Gen Chem 78, 1711–1718 (2008). https://doi.org/10.1134/S1070363208090120

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  • DOI: https://doi.org/10.1134/S1070363208090120

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