Advertisement

Russian Journal of General Chemistry

, Volume 89, Issue 5, pp 870–880 | Cite as

Synthesis and Structure of Geminally Activated Nitroethenes of the Indole Series

  • R. I. Baichurin
  • A. A. Fedorushchenko
  • N. I. Aboskalova
  • L. V. Baichurina
  • A. V. Felgendler
  • S. V. MakarenkoEmail author
Article
  • 15 Downloads

Abstract

A series of 2-(indol-3-yl)-1-nitroethenes containing an ester, acetyl, benzoyl, or cyano group in the geminal position with respect to the nitro group have been synthesized, and their structure has been studied by 1H, 13C−{1H} NMR, IR, and UV spectroscopy.

Keywords

indole gem-ethoxycarbonylnitroethene gem-acetylnitroethene gem-benzoylnitroethene gem-cyanonitroethene 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Supplementary material

11176_2019_3740_MOESM1_ESM.pdf (706 kb)
Synthesis and Structure of Geminally Activated Nitroethenes of the Indole Series

References

  1. 1.
    Perekalin, V.V., Sopova, A.S., and Lipina, E.S., Nepredel’nye nitrosoedineniya (Unsaturated Nitro Compounds), Leningrad: Khimiya, 1982.Google Scholar
  2. 2.
    Perekalin, V.V., Lipina, E.S., Berestovitskaya, V.M., and Efremov, D.A., Nitroalkenes. Conjugated Nitrocompounds, Chichester: Wiley, 1994.Google Scholar
  3. 3.
    Karakhanov, R.A., Kelarev, V.I., and Polivin, Yu.N., Russ. Chem. Rev., 1993, vol. 62, no. 2, p. 169. doi  https://doi.org/10.1070/RC1993v062n02ABEH000011 Google Scholar
  4. 4.
    Berestovitskaya, V.M., Baichurin, R.I., and Aboskalova, N.I., Sopryazhennye nitroeteny, geminal’no aktivirovannye slozhnoefirnoi, tsiano- i atsil’noi gruppami (Conjugated Nitroethenes Geminally Activated by Ester, Cyano, and Acyl Groups), St. Petersburg: Asterion, 2014.Google Scholar
  5. 5.
    Izbrannye metody sinteza i modifikatsii geterotsiklov. Khimiya sinteticheskikh indol’nykh sistem (Selected Methods of Synthesis and Modification of Heterocycles. Chemistry of Sunthetic Indole Systems), Kartsev, V.G., Ed., Moscow: IBS, 2004, vol. 3.Google Scholar
  6. 6.
    Shul’ts, E.E., Kartsev, V.G., and Tolstikov, G.A., Khimiya i biologicheskaya aktivnost’ indol’nykh alkaloidov (Chemistry and Biological Activity of Indole Alkaloids), Moscow: ICSPF, 2018.Google Scholar
  7. 7.
    Sharma, V., Kumar, P., and Pathak, D., J. Heterocycl. Chem., 2010, vol. 47, no. 3, p. 491. doi  https://doi.org/10.1002/jhet.349 Google Scholar
  8. 8.
    Kaushik, N.K., Kaushik, N., Attri, P., Kumar, N., Kim, C.H., Verma, A.K., and Choi, E.H., Molecules, 2013, vol. 18, no. 6, p. 6620. doi  https://doi.org/10.3390/molecules18066620 Google Scholar
  9. 9.
    Singh, T.P. and Singh, O.M., Mini Rev. Med. Chem., 2018, vol. 18, no. 1, p. 9. doi  https://doi.org/10.2174/1389557517666170807123201 Google Scholar
  10. 10.
    Mal’tsev, O.V., Beletskaya, I.P., and Zlotin, S.G., Russ. Chem. Rev., 2011, vol. 80, no. 11, p. 1067. doi RC2011v080n11ABEH004249Google Scholar
  11. 11.
    Mashkovskii, M.D., Lekarstvennye sredstva (Medicines), Moscow: Novaya Volna, 2012, 16th ed.Google Scholar
  12. 12.
    Zhungietu, G.I., Budylin, V.A., and Kost, A.N., Preparativnaya khimiya indola (Preparative Indole Chemistry), Kishinev: Shtiintsa, 1975Google Scholar
  13. 13.
    Baron, M., Metay, E., Lemaire, M., and Popowycz, F., J.Org. Chem., 2012, vol. 77, no. 7, p. 3598. doi  https://doi.org/10.1021/jo2026096 Google Scholar
  14. 14.
    Aksenov, A.V., Aksenov, N.A., Skomorokhov, A.A., Aksenova, I.V., Gryaznov, G.D., Voskressensky, L.G., and Rubin, M.A., Chem. Heterocycl. Compd., 2016, vol. 52, no. 11, p 923. doi  https://doi.org/10.1007/s10593-017-1988-x Google Scholar
  15. 15.
    Abdelwaly, A., Salama, I., Gomaa, M.S., and Helal, M.A., Med. Chem. Res., 2017, vol. 26, no. 12, p. 3173. doi  https://doi.org/10.1007/s00044-017-2011-x Google Scholar
  16. 16.
    Wang, Y.-C., Wang, J.-L., Burgess, K.S., Zhang, J.-W., Zheng, Q.-M., Pu, Y.-D., Yan, L.-J., and Chen, X.-B., RSC Adv., 2018, vol. 8, no. 11, p. 5702. doi  https://doi.org/10.1039/c7ra13207g Google Scholar
  17. 17.
    Zhmurov, P.A., Ushakov, P.Yu., Novikov, R.A., Sukhorukov, A.Yu., and Ioffe, S.L., Synlett, 2018, vol. 29, no. 14, p. 1871. doi  https://doi.org/10.1055/s-0037-1610213 Google Scholar
  18. 18.
    Dornow, A. and Menzel, H., Justus Liebigs Ann. Chem., 1954, vol. 588, no. 1, p. 40. doi  https://doi.org/10.1002/jlac.19545880105 Google Scholar
  19. 19.
    Aboskalova, N.I., Cand. Sci. (Chem.) Dissertation, Leningrad, 1971.Google Scholar
  20. 20.
    Aboskalova, N.I., Polyanskaya, A.S., and Perekalin, V.V., Dokl. Chem., 1967, vol. 176, no. 4, p. 861.Google Scholar
  21. 21.
    Vinograd, L.Kh. and Suvorov, N.N., Chem. Heterocycl. Compd., 1970, vol. 6, no. 11, p. 1403. doi  https://doi.org/10.1007/BF00476782 Google Scholar
  22. 22.
    Umezawa, S. and Zen, S., Bull. Chem. Soc. Jpn., 1963, vol. 36, no. 9, p. 1150. doi  https://doi.org/10.1246/bcsj.36.1150 Google Scholar
  23. 23.
    Baranov, M.S. and Yampolsky, I.V., Tetrahedron Lett., 2013, vol. 54, no. 7, p. 628. doi  https://doi.org/10.1016/j.tetlet.2012.11.132 Google Scholar
  24. 24.
    Dornow, A. and Sassenberg, W., Justus Liebigs Ann. Chem., 1957, vol. 602, no. 1, p. 14. doi  https://doi.org/10.1002/jlac.19576020102 Google Scholar
  25. 25.
    Zalukaev, L.P., Sintez i reaktsii al’fa-nitroketonov (Synthesis and Reactions of α-Nitro Ketones), Riga: Akad. Nauk Latv. SSR, 1958.Google Scholar
  26. 26.
    Babievskii, K.K., Doctoral (Chem.) Dissertation, Moscow, 1980.Google Scholar
  27. 27.
    Kochetkov, K.A., Babievskii, K.K., Belikov, V.M., Garbalinskaya, N.S., and Bakhmutov, V.I., Bull. Acad. Sci. USSR, Div. Chem. Sci., 1980, vol. 29, no. 3, p. 458. doi  https://doi.org/10.1007/BF00949634 Google Scholar
  28. 28.
    Lehnert, W., Tetrahedron, 1972, vol. 28, no. 3, p. 663. doi  https://doi.org/10.1016/0040-4020(72)84029-8 Google Scholar
  29. 29.
    Rodríguez, R., Viñets, I., Diez, A., Rubiralta, M., and Giralt, E., Synth. Commun., 1996, vol. 26, no. 16, p. 3029. doi  https://doi.org/10.1080/00397919608004608 Google Scholar
  30. 30.
    Rodríguez, R., Diez, A., Rubiralta, M., and Giralt, E., Heterocycles, 1996, vol. 43, no. 3, p. 513. doi  https://doi.org/10.3987/COM-95-7327 Google Scholar
  31. 31.
    Aboskalova, N.I., Polyanskaya, A.S., Perekalin, V.V., Demireva, Z.I., and Sokolova, L.N., J. Org. Chem. USSR, 1972, vol. 8, no. 6, p. 1349.Google Scholar
  32. 32.
    Polyanskaya, A.S., Perekalin, V.V., Aboskalova, N.I., and Sokolova, L.N., USSR Inventor’s Certificate no. 335246; Byull. Izobret., 1972, no. 13.Google Scholar
  33. 33.
    Fel’gendler, A.V., Aboskalova, N.I., and Berestovitskaya, V.M., Russ. J. Gen. Chem., 2000, vol. 70, no. 7, p. 1087.Google Scholar
  34. 34.
    Bakhareva, S.V., Cand. Sci. (Chem.) Dissertation, St. Petersburg, 2001.Google Scholar
  35. 35.
    Berestovitskaya, V.M., Aboskalova, N.I., Ishmaeva, E.A., Bakhareva, S.V., Berkova, G.A., Vereshchagina, Ya.A., Fel’gendler, A.V., and Fattakhova, G.R., Russ. J. Gen. Chem., 2001, vol. 71, no. 12, p. 1942. doi  https://doi.org/10.1023/A:1014200612456 Google Scholar
  36. 36.
    Baichurina, L.V., Baichurin, R.I., Aboskalova, N.I., and Berestovitskaya, V.M., Russ. J. Gen. Chem., 2010, vol. 80, no. 10, p. 2022. doi  https://doi.org/10.1134/S1070363210100221 Google Scholar
  37. 37.
    Velezheva, V.S., Erofeev, Yu.V., and Suvorov, N.N., J. Org. Chem. USSR, 1980, vol. 16, no. 10, p. 1839.Google Scholar
  38. 38.
    Baichurin, R.I., Baichurina, L.V., Aboskalova, N.I., and Berestovitskaya, V.M., Russ. J. Gen. Chem., 2013, vol. 83, no. 9, p. 1764. doi  https://doi.org/10.1134/S1070363213090223 Google Scholar
  39. 39.
    Baichurin, R.I., Aboskalova, N.I., Trukhin, E.V., and Berestovitskaya, V.M., Russ. J. Gen. Chem., 2015, vol. 85, no. 8, p. 1845. doi  https://doi.org/10.1134/S1070363215080101 Google Scholar
  40. 40.
    Wolinski, P., Jasiñski, R., Czamopismo Techniczne/Tech. Trans., 2018, vol. 2, p. 109. doi  https://doi.org/10.4467/2353737XCT.18.024.7997 Google Scholar
  41. 41.
    Polyanskaya, A.S., Perekalin, V.V., Aboskalova, N.I., Demireva, Z.I., Sokolova, L.N., and Abdulkina, Z.A., J. Org. Chem. USSR, 1979, vol. 15, no. 10, p. 859.Google Scholar
  42. 42.
    Shadrin, V.Yu., Cand. Sci. (Chem.) Dissertation, Leningrad, 1987.Google Scholar
  43. 43.
    Garming, A., Redwan, D., Gelbke, P., Kern, D., and Dierkes, U., Justus Liebigs Ann. Chem., 1975, no. 10, p. 1744. doi  https://doi.org/10.1002/jlac.197519751003
  44. 44.
    Ried, W. and Köhler, E., Justus Liebigs Ann. Chem., 1956, vol. 598, no. 2, p. 145. doi  https://doi.org/10.1002/jlac.19565980207 Google Scholar
  45. 45.
    Berestovitskaya, V.M., Baichurin, R.I., Aboskalova, N.I., Baichurina, L.V., Trukhin, E.V., Fel’gendler, A.V., and Gensirovskaya, M.A., Russ. J. Gen. Chem., 2016, vol. 86, no. 6, p. 1266. doi  https://doi.org/10.1134/S1070363216060086 Google Scholar
  46. 46.
    Berestovitskaya, V.M., Ishmaeva, E.A., Litvinov, I.A., Vasil’eva, O.S., Vereshchagina, Ya.A., Ostroglyadov, E.S., Fattakhova, G.R., Beskrovnyi, D.V., and Aleksandrova, S.M., Russ. J. Gen. Chem., 2004, vol. 74, no. 7, p. 1108. doi  https://doi.org/10.1023/B:RUGC.0000045874.46434.ea Google Scholar
  47. 47.
    Bulatova, N.N. and Suvorov, N.N., Chem. Heterocycl. Compd., 1969, vol. 5, no. 5, p. 602. doi  https://doi.org/10.1007/BF00957368 Google Scholar
  48. 48.
    Young, E.H.P., J. Chem. Soc., 1958, no. 10, p. 3493. doi  https://doi.org/10.1039/JR9580003493
  49. 49.
    Ionin, B.I., Ershov, B.A., and Kol’tsov, A.I., YaMR-spektroskopiya v organicheskoi khimii (NMR Spectroscopy in Organic Chemistry), Leningrad: Khimiya, 1983.Google Scholar
  50. 50.
    Troschütz, R. and Grün, L., Archiv Pharm., 1993, vol. 326, no. 11, p. 857. doi  https://doi.org/10.1002/ardp.19933261104 Google Scholar
  51. 51.
    Babievskii, K.K., Bakhmutov, V.I., Kochetkov, K.A., Burmistrov, V.A., and Belikov, V.M., Bull. Acad. Sci. USSR, Div. Chem. Sci., 1977, vol. 26, no. 2, p. 384. doi  https://doi.org/10.1007/BF00921860 Google Scholar
  52. 52.
    Aboskalova, N.I., Babievskii, K.K., Belikov, V.M., Perekalin, V.V., and Polyanskaya, A.S., J. Org. Chem. USSR, 1973, vol. 9, no. 5, p. 1082.Google Scholar

Copyright information

© Pleiades Publishing, Ltd. 2019

Authors and Affiliations

  • R. I. Baichurin
    • 1
  • A. A. Fedorushchenko
    • 1
  • N. I. Aboskalova
    • 1
  • L. V. Baichurina
    • 2
  • A. V. Felgendler
    • 2
  • S. V. Makarenko
    • 1
    Email author
  1. 1.Herzen State Pedagogical University of RussiaSt. PetersburgRussia
  2. 2.Kirov Military Medical AcademySt. PetersburgRussia

Personalised recommendations