Advertisement

Russian Journal of Organic Chemistry

, Volume 48, Issue 9, pp 1200–1209 | Cite as

Reactions of N- and C-alkenylanilines: X. Synthesis of 2-vinyldihydroindoles from 4-methyl-2-(pent-3-en-2-yl)aniline

  • G. G. Mazgarova
  • A. M. Absalyamova
  • R. R. Gataullin
Article

Abstract

2-(1-Iodoethyl)-3,5-dimethyl-1-(4-methylphenylsulfonyl)-2,3-dihydro-1H-indole reacted with pyridine, piperidine, N-alkylpiperidines, and dimethylformamide to give dehydrohalogenation and halogen substitution products whose ratio depended on the reagent structure. Heating of 2-(1-iodoethyl)-3,5-dimethyl-1-methylsulfonyl-2,3-dihydro-1H-indole with piperidine resulted in the formation of only dehydroiodination products.

Keywords

Piperidine Sodium Hydrogen Carbonate Sodium Tetrahydridoborate Compound Xviii Iodoethyl 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    Skladchikov, D.A., Suponitskii, K.Yu., Abdrakhmanov, I.B., and Gataullin, R.R., Russ. J. Org. Chem., 2012, vol. 48, p. 957.CrossRefGoogle Scholar
  2. 2.
    Anisimova, N.A., Berkova, G.A., Ladygin, V.V., and Berestovitskaya, V.M., Russ. J. Org. Chem., 2006, vol. 42, p. 1246.CrossRefGoogle Scholar
  3. 3.
    Balasubramanian, T. and Balasubramanian, K.K., J. Chem. Soc., Chem. Commun., 1994, p. 1237.Google Scholar
  4. 4.
    Jones, R.A., Fresneda, P.M., Saliente, T.A., and Arqves, J.S., Tetrahedron, 1984, vol. 40, p. 4837.CrossRefGoogle Scholar
  5. 5.
    Rogers, M.M., Wendlandt, J.E., Guzei, I.A., and Stahl, S.S., Org. Lett., 2006, vol. 8, p. 2257.CrossRefGoogle Scholar
  6. 6.
    Gonzalez-Perez, P., Perez-Serrano, L., Casarrubios, L., Dominguez, G., and Perez-Castells, J., Tetrahedron Lett., 2002, vol. 43, p. 4756.CrossRefGoogle Scholar
  7. 7.
    Orr, S.T.M., Tian, J., Niggemann, M., and Martin, S.M., Org. Lett., 2011, vol. 13, p. 5104.CrossRefGoogle Scholar
  8. 8.
    Namba, K., Nakagawa, Y., Yamamoto, H., Imagawa, H., and Nishizawa, M., Synlett, 2008, p. 1719.Google Scholar
  9. 9.
    O’Connor, J.M., Stallman, B.J., Clark, W.G., Shu, A.Y.L., Spada, R.E., Stevenson, T.M., and Dieck, H.A., J. Org. Chem., 1983, vol. 48, p. 807.CrossRefGoogle Scholar
  10. 10.
    Larock, R.C., Hightower, T.R., Hasvold, L.A., and Peterson, K.R., J. Org. Chem., 1996, vol. 61, p. 3584.CrossRefGoogle Scholar
  11. 11.
    Gataullin, R.R., Minnigulov, F.F., Fatykhov, A.A., Spirikhin, L.V., and Abdrakhmanov, I.B., Russ. J. Org. Chem., 2002, vol. 38, p. 31.CrossRefGoogle Scholar
  12. 12.
    Panasenko, A., Elementarnyi kurs po yadernomu magnitnomu rezonansu (Introductory Lectures on Nuclear Magnetic Resonance), Kishinev, 1999.Google Scholar

Copyright information

© Pleiades Publishing, Ltd. 2012

Authors and Affiliations

  • G. G. Mazgarova
    • 1
  • A. M. Absalyamova
    • 1
  • R. R. Gataullin
    • 1
  1. 1.Institute of Organic Chemistry, Ufa Research CenterRussian Academy of SciencesUfaBashkortostan, Russia

Personalised recommendations