Synthesis and Structure of Geminally Activated Nitroethenes of the Indole Series

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.

This is a preview of subscription content, log in to check access.

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

    Article  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.

  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

    CAS  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

    CAS  Article  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

    CAS  PubMed  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 RC2011v080n11ABEH004249

    Article  Google 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, 1975

    Google 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

    CAS  Article  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

    CAS  Article  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

    CAS  Article  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

    CAS  Article  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

    CAS  Article  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

    CAS  Article  Google Scholar 

  19. 19.

    Aboskalova, N.I., Cand. Sci. (Chem.) Dissertation, Leningrad, 1971.

  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

    Article  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

    CAS  Article  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

    CAS  Article  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

    CAS  Article  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.

  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

    CAS  Article  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

    Article  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

    Article  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.

  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.

  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

    CAS  Article  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

    CAS  Article  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

    CAS  Article  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

    CAS  Article  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.

  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

    CAS  Article  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

    CAS  Article  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

    CAS  Article  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

    Article  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

    Article  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

    Article  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 

Download references

Author information

Affiliations

Authors

Corresponding author

Correspondence to S. V. Makarenko.

Additional information

Russian Text © The Authors(s), 2019, published in Zhurnal Obshchei Khimii, 2019, Vol. 89, No. 5, pp. 671–683.

Supporting Information

Rights and permissions

Reprints and Permissions

About this article

Verify currency and authenticity via CrossMark

Cite this article

Baichurin, R.I., Fedorushchenko, A.A., Aboskalova, N.I. et al. Synthesis and Structure of Geminally Activated Nitroethenes of the Indole Series. Russ J Gen Chem 89, 870–880 (2019). https://doi.org/10.1134/S1070363219050037

Download citation

Keywords

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