Russian Journal of Organic Chemistry

, Volume 49, Issue 10, pp 1486–1490 | Cite as

Synthesis, structure, and heck cyclization of the syn- and anti-atropisomers of N-acyl-N-(4-methyl-3,6-dihydro-2H-pyran-3-yl)-2-iodo-4,6-dimethylaniline

  • D. A. Skladchikov
  • K. Yu. Suponitskii
  • R. R. Gataullin


The reaction of 2-iodo-2,4-dimethylaniline with 3,4-dibromo-4-methyltetrahydro-2H-pyran, followed by treatment with acetyl bromide or 4-nitrobenzoyl chloride, gave syn- and anti-atropisomers of N-(2-iodo-4,6-dimethylphenyl)-N-(4-methyl-3,6-dihydro-2H-pyran-3-yl)acetamide and N-(2-iodo-4,6-dimethylphenyl)-N-(4-methyl-3,6-dihydro-2H-pyran-3-yl)-4-nitrobenzamide. Heating of the acetamide derivative with palladium(II) acetate in the presence of copper(II) acetate and N,N,N′,N′-tetramethylethane-1,2-diamine resulted in heterocyclization to N-acetyl-4a,6,8-trimethyl-1,4a,9,9a-tetrahydropyrano[3,4-b]indole.


EtOAc Dimethylaniline Dimethylphenyl Acetyl Bromide Nitrobenzamide 
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.


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.


  1. 1.
    LaPorte, M.G., Draper, T.L., Miller, L.M., Blackledge, C.W., Leister, L.K., Amparo, E., Hussey, A.R., Young, D.C., Chunduru, S.K., Benetatos, C.A., Rhodes, G., Gopalsamy, A., Herbertz, T., Burns, C.J., and Condon, S.C., Bioorg. Med. Chem. Lett., 2010, vol. 20, p. 2968.CrossRefGoogle Scholar
  2. 2.
    Gopalsamy, A., Lim, K., Ciszewski, G., Park, K., Ellingboe, J.W., Bloom, J., Insaf, S., Upeslacis, J., Mansour, T.S., Krishnamurthy, G., Damarla, M., Pyatski, Y., Ho, D., Howe, A.J.M., Orlowski, M., Feld, B., and O’Connell, J., J. Med. Chem., 2004, vol. 47, p. 6603.CrossRefGoogle Scholar
  3. 3.
    Ngi, S.I., Guilloteau, V., Abarbri, M., and Thibonnet, J., J. Org. Chem., 2011, vol. 76, p. 8347.CrossRefGoogle Scholar
  4. 4.
    Zhang, J.-W., Cai, Q., Shi, X.-B., Zhang, W., and You, S.-L., Synlett, 2011, p. 1239.Google Scholar
  5. 5.
    Skladchikov, D.A., Fatykhov, A.A., and Gataullin, R.R., Russ. J. Org. Chem., 2012, vol. 48, p. 383.CrossRefGoogle Scholar
  6. 6.
    Kosynkin, D.V. and Tour, J.M., Org. Lett., 2001, vol. 3, p. 991.Google Scholar
  7. 7.
    Allen, F.H., Kennard, O., Watson, D.G., Brammer, L., Orpen, A.G., and Taylor, R., J. Chem. Soc., Perkin Trans. 2, 1987, p. S1.Google Scholar
  8. 8.
    APEX2 and SAINT, Madison, Wisconsin, USA: Bruker AXS, 2005.Google Scholar
  9. 9.
    Sheldrick, G.M., Acta Crystallogr., Sect. A, 2008, vol. 64, p. 112.CrossRefGoogle Scholar

Copyright information

© Pleiades Publishing, Ltd. 2013

Authors and Affiliations

  • D. A. Skladchikov
    • 1
  • K. Yu. Suponitskii
    • 2
  • R. R. Gataullin
    • 1
  1. 1.Institute of Organic Chemistry, Ufa Research CenterRussian Academy of SciencesUfaBashkortostan, Russia
  2. 2.Nesmeyanov Institute of Organoelement CompoundsRussian Academy of SciencesMoscowRussia

Personalised recommendations