Russian Journal of Organic Chemistry

, Volume 47, Issue 3, pp 402–404 | Cite as

Three-component synthesis of spiro compounds with a carbamate functionality

  • A. V. Velikorodov
  • O. Yu. Poddubnyi
  • O. O. Krivosheev
  • O. L. Titova
Article

Abstract

1,3-Dipolar cycloaddition of methyl 4-[2-(2-oxo-1,2-dihydro-3H-indol-3-ylidene)acetyl]phenylcarbamate to non-stabilized azomethine ylides generated by decarboxylation of α-amino acid (sarcosine and proline) adducts with ketones (isatin and ninhydrin) occurred regioselectively with formation of the corresponding spiro compounds having a carbamate moiety.

Keywords

Isatin Sarcosine Spiro Compound Phenylcarbamate Oxoethylidene 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    Velikorodov, A.V., Imasheva, N.M., Kuanchalieva, A.K., and Poddubnyi, O.Yu., Russ. J. Org. Chem., 2010, vol. 46, p. 971.CrossRefGoogle Scholar
  2. 2.
    Serov, A.B., Cand. Sci. (Chem.) Dissertation, Nizhnii Novgorod, 2007.Google Scholar
  3. 3.
    Serov, A.B., Kartsev, V.G., Alexandrov, Yu.A., and Dolgushin, F.M., Rus. Chem. Bull., Int. Ed., 2005, vol. 54, p. 2432.CrossRefGoogle Scholar
  4. 4.
    Manikandan, S., Mohamed Ashraf, M., and Raghunathan, R., Synth. Commun., 2001, vol. 31, p. 3593.CrossRefGoogle Scholar
  5. 5.
    Manian Rathna Durga, R.S., Jayadevan Jayashankaran, S., Kumar, S.S., and Raghunathan, R., Tetrahedron Lett., 2006, vol. 47, p. 829.CrossRefGoogle Scholar
  6. 6.
    Casaschi, A., Desimoni, G., Faita, G., Invernizzi, A.G., and Grunanger, P., Gazz. Chim. Ital., 1993, vol. 123, p. 137.Google Scholar
  7. 7.
    Guan, Y., Green, M.A., and Bergstrom, D.E., J. Comb. Chem., 2000, vol. 2, p. 297.CrossRefGoogle Scholar
  8. 8.
    Kornet, M.J. and Thio, A.P., J. Med. Chem., 1976, vol. 19, p. 892.CrossRefGoogle Scholar

Copyright information

© Pleiades Publishing, Ltd. 2011

Authors and Affiliations

  • A. V. Velikorodov
    • 1
  • O. Yu. Poddubnyi
    • 1
  • O. O. Krivosheev
    • 1
  • O. L. Titova
    • 1
  1. 1.Astrakhan State UniversityAstrakhanRussia

Personalised recommendations