Skip to main content
Log in

Reactions of caryophyllene, isocaryophyllene, and their epoxy derivatives with acetonitrile under ritter reaction conditions

  • Published:
Russian Journal of Organic Chemistry Aims and scope Submit manuscript

Abstract

Acid-catalyzed reactions between acetonitrile and caryophyllene, isocaryophyllene, caryophyllene 4β, 5α-epoxide, and isocaryophyllene 4β,5β-epoxide affording optically active amides with a tricyclic skeleton were investigated.

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

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

REFERENCES

  1. Yarovaya, O.I., Korchagina, D.V., Salomatina, O.V., Polovinka, M.P., and Barkhash, V.A., Mendeleev Commun., 2003, no. 1, p. 28.

  2. Boyd, G.V., in Comprehensive Heterocyclic Chemistry II, Katrizky, A.R., Rees, C.W., and Scriven, E.F.V., Eds., Oxford: Pergamon, 1996, vol. 6, p. 229.

    Google Scholar 

  3. Koval’skaya, S.S. and Kozlov, N.G., Zh. Org. Khim., 1994, vol. 30, p. 1335.

    Google Scholar 

  4. Amigo, C.F.D., Collado, I.G., Hanson, J.R., Hernandez-Galan, R., Hitchcock, P.B., Macias-Sanchez, A.J., and Mobbs, D.J., J. Org. Chem., 2001, vol. 66, p. 4327.

    Google Scholar 

  5. Aleu, J., Hernandez-Galan, R., Hanson, J.R., Hitchcock, P.B., Collado, I.G.., J. Chem. Soc., Perkin Trans. I, 1999, p. 727.

    Google Scholar 

  6. Polovinka, M.P, Korchagina, D.V., Gatilov, Yu.V., Bagrianskaya, I.Yu., Barkhash, V.A., Shcherbukhin, V.V., Zefirov, N.S., Perutskii, V.B., Ungur, N.D., and Vlad, P.F., J. Org. Chem., 1994, vol. 59, p. 1509.

    Google Scholar 

  7. Khomenko, T.M., Korchagina, D.V., Gatilov, Yu.V., Bagryanskaya, I.Yu., Rybalova, T.V., Sal’nikov, G.E., Mamatyuk, V.I., Dubovenko, Zh.V., and Barkhash, V.A., Zh. Org. Khim., 1991, vol. 27, p. 570.

    Google Scholar 

  8. Nisnevich, G.A., Korchagina, D.V., Makal’skii, V.A., Dubovenko, Zh.V, and Barkhash, V.A., Zh. Org. Khim., 1993, vol. 29, p. 524.

    Google Scholar 

  9. Collado, I.J., Hanson, J.R., and Macias-Sanchez, A.J., Nat. Prod. Rep., 1998, vol. 15, p. 187.

    Google Scholar 

  10. Fomenko, V.V., Korchagina, D.V., Salakhutdinov, N.F., and Barkhash, V.A., Helv. Shim. Acta, 2001, vol. 84, p. 3477.

    Google Scholar 

  11. Tkachev, A.V., Mamatyuk, V.I., and Dubovenko, Zh.V, Zh. Org. Khim., 1990, vol. 26, p. 1698.

    Google Scholar 

  12. Aebi, A., Barton, D.H.R., Burgstahler, A.W., and Lindsey, A.S., J. Chem. Soc., 1954, vol. 12, p. 4659.

    Google Scholar 

  13. Collado, I.J., Hanson, J.R., and Macias-Sanchez, A.J., Tetrahedron, 1996, vol. 52, p. 7961.

    Google Scholar 

  14. Rachlin, S., US Patent 3621070; Ref. Zh. Khim., 1971, 192.14, R448.

  15. Bombarda, I., Gaydou, E.M., Smadja, J., and Faure, R., Bull. Soc. Chim., 1995, vol. 132, p. 836.

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Additional information

Translated from Zhurnal Organicheskoi Khimii, Vol. 40, No. 11, 2004, pp. 1641–1646.

Original Russian Text Copyright © 2004 by Yarovaya, Korchagina, Rybalova, Gatilov, Polovinka, Barkhash.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Yarovaya, O.I., Korchagina, D.V., Rybalova, T.V. et al. Reactions of caryophyllene, isocaryophyllene, and their epoxy derivatives with acetonitrile under ritter reaction conditions. Russ J Org Chem 40, 1593–1598 (2004). https://doi.org/10.1007/s11178-005-0065-6

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11178-005-0065-6

Keywords

Navigation