Skip to main content
SpringerLink
Log in

Experimental and theoretical study on the reaction of bicyclo[2.2.1]hept-5-en-endo-2-ylmethanamine with glycidyl ethers

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

Abstract

Reactions of bicyclo[2.2.1]hept-5-en-endo-2-ylmethanamine with phenyl, 4-methylphenyl, 3-methylphenyl, 2-methylphenyl, 4-methoxyphenyl, cyclohexyl, and cyclohexenyl 2,3-epoxypropyl ethers gave the corresponding N-mono- and N,N-bis(3-R-oxy-2-hydroxypropyl) derivatives. The structure of the newly synthesized amino alcohols and regioselectivity of oxirane ring opening were determined by IR spectroscopy, 1H and 13C NMR, and mass spectrometry. The reaction mechanism was studied by quantum chemistry at the PCM/B3LYP/6-31G(d) level of theory.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Bergmeier, S.C., Tetrahedron, 2000, vol. 56, p. 2561; Lait, S.M., Rankic, D.A., and Keay, B.A., Chem. Rev., 2007, vol. 107, p. 767; Ager, D.J., Prakash, I., and Schaad, D.R., Chem. Rev., 1996, vol. 96, p. 835; Kas’yan, L.I., Okovityi, S.I., and Kas’yan, A.O., Russ. J. Org. Chem., 2004, vol. 40, p. 1; Kas’yan, L.I. and Pal’chikov, V.A., Russ. J. Org. Chem., 2010, vol. 46, p. 1; Kas’yan, L.I., Kas’yan, A.O., Okovityi, S.I., and Tarabara, I.N., Aminy s karkasnymi fragmentami i ikh proizvodnye (Amines with Cage-Like Fragments and Their Derivatives), Dnepropetrovsk: Dnepropetr. Univ., 2009; Mashkovskii, M.D., Lekarstvennye sredstva (Drugs), Moscow: Novaya Volna, 2002.

    Article  CAS  Google Scholar 

  2. Tandon, V.K., Kumar, M., Awasthi, A.K., Saxena, H.O., and Goswamy, G.K., Bioorg. Med. Chem. Lett., 2004, vol. 14, p. 3177.

    Article  CAS  Google Scholar 

  3. Muthukrishnan, M., Garud Dinesh, R., Joshi, R.R., and Joshi, R.A., Tetrahedron, 2007, vol. 63, p. 1872; Bose, D., Synthesis, 2005, vol. 14, p. 2345.

    Article  CAS  Google Scholar 

  4. Pandey, D., Katti, S.B., Haq, W., and Tripathi, C.K.M., Bioorg. Med. Chem., 2004, vol. 12, p. 3807.

    Article  CAS  Google Scholar 

  5. Schenone, S., Bruno, O., Ranise, A., Bondavalli, F., Filippelli, W., Falcone, G., and Rinaldi, B., Il Farmaco, 2000, vol. 55, p. 495; Satyanarayana, M., Tiwari, P., Tripathi, B.K., Srivastava, A.K., and Pratap, R., Bioorg. Med. Chem., 2004, vol. 12, p. 883.

    Article  CAS  Google Scholar 

  6. Gavai, A.V., Bioorg. Med. Chem. Lett., 2005, vol. 15, p. 5478.

    Article  CAS  Google Scholar 

  7. Krushinski, J.H., Bioorg. Med. Chem. Lett., 2007, vol. 17, p. 5600.

    Article  CAS  Google Scholar 

  8. Alder, K., Heimbach, K., and Reubke, R., Chem. Ber., 1958, vol. 91, p. 1516.

    Article  CAS  Google Scholar 

  9. Zlenko, E.T., Mamchur, V.I., Kas’yan, L.I., Kas’yan, A.O., and Karpenko, D.V., Zaporozh. Med. Zh., 2004, vol. 1, no. 22, p. 48; Kas’yan, L.I., Zlenko, E.T., Turov, A.V., Prid’ma, S.A., and Kas’yan, A.O., Zh. Org. Farm. Khim., 2008, vol. 6, no. 3, p. 76; Zlenko, E.T., Kas’yan, L.I., Mamchur, V.I., Kas’yan, A.O., Prid’ma, S.A., Pal’chikov, V.A., and Karat, L.D., Zh. Org. Farm. Khim., 2009, vol. 7, no. 1, p. 64; Zlenko, N.T., Kasyan, L.I., Palchikov, V.A., Pridma, S.A., and Oprishko, V.I., Book of Abstracts of the IXth World Congress of Biological Psychiatry, Paris, 2009, p. 433.

    Google Scholar 

  10. Kasyan, L.I., Zlenko, H.T., Golodayeva, E.A., Kasyan, A.O., and Karpenko, D.V., Book of Abstracts of Joint Meeting on Medicinal Chemistry, Krakow, 2003, p. 139.

  11. Nakanishi, K., Infrared Absorption Spectroscopy. Practical, San Francisco: Holden-Day, 1962.

    Google Scholar 

  12. Zefirov, N.S. and Sokolov, V.I., Usp. Khim., 1967, vol. 36, p. 243.

    CAS  Google Scholar 

  13. Claridge, T.D.W., High Resolution NMR Techniques in Organic Chemistry, Oxford: Pergamon, 1999.

    Google Scholar 

  14. Parker, R.E. and Isaacs, N.S., Chem. Rev., 1959, vol. 59, p. 737; Kirk, D.N., Chem. Ind., 1973, p. 109.

    Article  CAS  Google Scholar 

  15. Kas’yan, A.O., Golodaeva, E.A., Tsygankov, A.V, and Kas’yan, L.I., Russ. J. Org. Chem., 2002, vol. 38, p. 1606; Kas’yan, L.I., Golodaeva, E.A., Nadtoka, M.I., and Kas’yan, A.O., Visn. Dnipropetr. Univ., Khim., 2002, no. 8, p. 41; Kas’yan, L.I., Kostenko, L.I., Golodaeva, E.A., Radchenko, E.D., Bondarenko, Ya.S., and Prid’ma, S.A., Vopr. Khim. Khim. Tekhnol., 2008, no. 2, p. 16; Kas’yan, L.I., Batog, A.E., Kas’yan, A.O., Gaponova, R.G., Savel’eva, O.A., and Golodaeva, E.A., Vopr. Khim. Khim. Tekhnol., 2000, no. 1, p. 34; Kas’yan, L.I., Golodaeva, E.A., Kas’yan, A.O., Isaev, A.K., and Bondarenko, Ya.S., Visn. Dn?propetr. Univ., Khim., 2007, no. 10, p. 48.

    Article  Google Scholar 

  16. Kas’yan, L.I., Prid’ma, S.A., Turov, A.V., Pal’chikov, V.A., Kas’yan, A.O., and Karat, L.D., Russ. J. Org. Chem., 2009, vol. 45, p. 505.

    Article  Google Scholar 

  17. Becke, A.D., J. Chem. Phys., 1993, vol. 98, p. 5648; Lee, C., Yang, W., and Parr, R.G., Phys. Rev. B, 1988, vol. 37, p. 785; Hariharan, P.C. and Pople, J.A., Chem. Phys. Lett., 1972, vol. 66, p. 217; Cammi, R., Mennucci, B., and Tomasi, J., J. Chem. Phys., 1999, vol. 110, p. 7627.

    Article  CAS  Google Scholar 

  18. Kas’yan, L.I., Prid’ma, S.A., Isaev, A.K., and Karat, L.D., Abstracts of Papers, XI Mezhdunarodnaya nauchno-tekhnicheskaya konferentsiya “Perspektivy razvitiya khimii i prakticheskogo primeneniya alitsiklicheskikh soedinenii” (XIth Int. Scientific and Technical Conf. “Perspectives in the Development of Chemistry and Practical Applications of Alicyclic Compounds”), Volgograd, 2008, p. 147.

Download references

Author information

Authors and Affiliations

  1. Oles’ Gonchar Dnepropetrovsk National University, pr. Gagarina 72, Dnepropetrovsk, 49010, Ukraine

    L. I. Kas’yan, S. A. Prid’ma, V. A. Pal’chikov & S. I. Okovityi

  2. Shevchenko Kiev National University, Kiev, Ukraine

    A. V. Turov

  3. Ukrainian Research Institute of Plastics, Donetsk, Ukraine

    L. D. Karat

  4. Vinnichenko Kirovograd State Pedagogical University, Kirovograd, Ukraine

    L. K. Svyatenko

Authors
  1. L. I. Kas’yan
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. A. V. Turov
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. L. D. Karat
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. S. A. Prid’ma
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. V. A. Pal’chikov
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. L. K. Svyatenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. S. I. Okovityi
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to V. A. Pal’chikov.

Additional information

Original Russian Text © L.I. Kas’yan, A.V. Turov, L.D. Karat, S.A. Prid’ma, V.A. Pal’chikov, L.K. Svyatenko, S.I. Okovityi, 2011, published in Zhurnal Organicheskoi Khimii, 2011, Vol. 47, No. 1, pp. 77–84.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Kas’yan, L.I., Turov, A.V., Karat, L.D. et al. Experimental and theoretical study on the reaction of bicyclo[2.2.1]hept-5-en-endo-2-ylmethanamine with glycidyl ethers. Russ J Org Chem 47, 74–82 (2011). https://doi.org/10.1134/S1070428011010088

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428011010088

Keywords

Search

Navigation