Skip to main content
SpringerLink
Log in

Atropisomeric N-acyl-N-(cyclopentenylphenyl)glycines in the synthesis of oxazolo[3,4-a]benzoxazocinones

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

Abstract

Intramolecular [3+2]-cycloaddition was studied of munchnones generated at heating syn- and anti-atropisomers of N-acyl-N-[6-methyl-2-(cyclopent-2-en-1-yl)phenyl]glycines with acetic anhydride. By spectral and X-ray diffraction analysis syn-isomers of acids and tetrahydro-1,4,7-methanetriyl[1,3]oxazolo[3,4-a][1]- bensazocin-3(3aH)-ones were identified.

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. Nakajima, R., Yamamoto, N., Hirayama, S., Iwai, T., Saitoh, A., Nagumo, Y., Fujii, H., and Nagase, H., Bioorg. Med. Chem., 2015, vol. 23, p. 6271. doi 10.1016/j.bmc.2015.08.036

    Article  CAS  Google Scholar 

  2. Hajicek, J., Taimr, J., and Budesinsky, M., Tetrahedron Lett., 1998, vol. 39, p. 505. doi 10.1016/S0040-4039(97)10588-3

    Article  CAS  Google Scholar 

  3. Kariba, R.M., Houghton, P.J., and Yenesew, A., J. Nat. Prod., 2002, vol. 65, p. 566. doi 10.1021/np010298m

    Article  CAS  Google Scholar 

  4. Gómez-Ayala, S., Castrillyn, J.A., Palma, A., Leal, S.M., Escobar, P., and Bahsas, A., Bioorg. Med. Chem., 2010, vol. 18, p. 4721. doi 10.1016/j.bmc.2010.05.018

    Article  Google Scholar 

  5. Volla, C.M.R., Fava, E., Atodiresei, I., and Rueping, M., Chem. Commun., 2015, vol. 51, p. 15788. doi 10.1039/C5CC05209B

    Article  CAS  Google Scholar 

  6. Umstead, W.J., Mukhina, O.A., and Kutateladze, A.G., Eur. J. Org. Chem., 2015, p. 2205. doi 10.1002/ejoc.201403620

    Google Scholar 

  7. Kutsumura, N., Nakajima, R., Koyama, Y., Miyata, Y., Saitoh, T., Yamamoto, N., Iwata, S., Fujii, H., and Nagase, H., Bioorg. Med. Chem. Lett., 2015, vol. 23, p. 4890. doi 10.1016/j.bmcl.2015.06.002

    Article  Google Scholar 

  8. Zhou, J. and Magomedov, N.A., J. Org. Chem., 2007, vol. 72, p. 3808. doi 10.1021/jo070144x

    Article  CAS  Google Scholar 

  9. Ransborg, L.K., Overgaard, M., Hejmanowska, J., Barfüsser, S., Jorgensen, K.A., and Jukasz, A., J. Org. Lett., 2014, vol. 16, p. 4182. doi 10.1021/ol501882x

    Article  CAS  Google Scholar 

  10. Wang, X., Xia, D., Tan, L., Chen, H., Huang, H., Song, H., and Qin, Y., Chem. Eur. J., 2015, vol. 21, p. 14602. doi 10.1002/chem.201502869

    Article  CAS  Google Scholar 

  11. Meier, H. and Heimgartner, H., Helv. Chim. Acta, 1977, vol. 60, p. 1087. doi 10.1002/hlca.19770600333

    Article  CAS  Google Scholar 

  12. Meier, H., Heimgartner, H., and Schmid, H., Helv. Chim. Acta, 1986, vol. 69, p. 927. doi 10.1002/hlca.19860690421

    Article  CAS  Google Scholar 

  13. Padwa, A., Gingrich, H.L., and Lim, R., Tetrahedron Lett., 1980, vol. 21, p. 3419. doi 10.1016/S0040-4039(00)78704-1

    Article  CAS  Google Scholar 

  14. Padwa, A., Gingrich, H.L., and Lim, R., J. Org. Chem., 1982, vol. 47, p. 2447. doi 10.1021/jo00133a041

    Article  CAS  Google Scholar 

  15. Padwa, A., Lim, R., MacDonald, J.G., Gingrich, H.L., and Kellar, S.M., J. Org. Chem., 1985, vol. 50, p. 3816. doi 10.1021/jo00220a027

    Article  CAS  Google Scholar 

  16. Mazgarova, G.G., Fatykhov, A.A., and Gataullin, R.R., Russ. J. Org. Chem., 2014, vol. 50, p. 1155. doi 10.1134/S1070428014080144

    Article  CAS  Google Scholar 

  17. Mazgarova, G.G., Fatykhov, A.A., and Gataullin, R.R., Russ. J. Org. Chem., 2014, vol. 50, p. 1346. doi 10.1134/S1070428014090188

    Article  CAS  Google Scholar 

  18. Acosta, L.M., Palma, A., and Bahsas, A., Tetrahedron, 2010, vol. 66, p. 8392. doi 10.1016/j.tet.2010.08.067

    Article  CAS  Google Scholar 

  19. Miao, Q. and Sun, H.-L., Chin. J. Org. Chem., 2016, vol. 36, p. 913. doi 10.6023/cjoc201511047

    Article  CAS  Google Scholar 

  20. Bizhanova, G.G., Suponitsky, K.Yu., Vakhitova, Yu.V., and Gataullin, R.R., Tetrahedron, 2017, vol. 73, p. 109. doi 10.1016/j.tet.2016.11.038

    Article  CAS  Google Scholar 

  21. Guthrie, D.B., Geib, S.J., and Curran, D.P., J. Am. Chem. Soc., 2011, vol. 133, p. 115. doi 10.1021/ja108795x

    Article  CAS  Google Scholar 

  22. Bruch, A., Fruhlich, R., Grimme, S., Studer, A., and Curran, D.P., J. Am. Chem. Soc., 2011, vol. 133, p. 16270. doi 10.1021/ja2070347

    Article  CAS  Google Scholar 

  23. Skladchikov, D.A., Fatykhov, A.A., and Gataullin, R.R., Russ. J. Org. Chem., 2012, vol. 48, p. 383. doi 10.1134/S1070428012030086

    Article  CAS  Google Scholar 

  24. Skladchikov, D.A., Suponitskii, K.Yu., and Gataullin, R.R., Russ. J. Org. Chem., 2013, vol. 49, p. 1486. doi 10.1134/S107042801310014X

    Article  CAS  Google Scholar 

  25. Skladchikov, D.A. and Gataullin, R.R., Russ. J. Gen. Chem., 2013, vol. 83, p. 368. doi 10.1134/S1070363213020217

    Article  CAS  Google Scholar 

  26. Ichikawa, M., Yokomizo, A., Itoh, M., Haginoya, N., Sugita, K., Usui, H., Terayama, K., and Kanda, A., Bioorg. Med. Chem., 2011, vol. 19, p. 5207. doi 10.1016/j.bmc.2011.07.007

    Article  CAS  Google Scholar 

  27. Kumarasamy, E., Raghunathan, R., Sibi, M.P., and Sivaguru, J., Chem. Rev., 2015, vol. 115, p. 11239. doi 10.1021/acs.chemrev.5b00136

    Article  CAS  Google Scholar 

  28. Abdrakhmanov, I.B., Sharafutdinov, V.M., and Tolstikov, G.A., Bull. Acad. Sci. USSR., Div. Chem. Sci., 1982, vol. 31, p. 1910. doi 10.1007/BF00952402

    Article  Google Scholar 

  29. Agilent, CrysAlis PRO, Agilent Technologies, 2012, Yarnton, Oxfordshire, England.

    Google Scholar 

  30. Sheldrick, G.M., Acta Cryst., Sect. A., 2008, vol. 64, p. 112. doi 10.1107/S0108767307043930

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Ufa Institute of Chemistry, Russian Academy of Sciences, pr. Oktyabrya 71, Ufa, 450054, Russia

    R. R. Gataullin & A. A. Fatykhov

  2. Ufa Institute of Biology, Russian Academy of Sciences, Ufa, Russia

    Z. A. Ibatullina

  3. Institute of Petrochemistry and Catalysis, Russian Academy of Sciences, Ufa, Russia

    E. S. Meshcheryakova & L. M. Khalilov

Authors
  1. R. R. Gataullin
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Z. A. Ibatullina
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. E. S. Meshcheryakova
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. A. A. Fatykhov
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. L. M. Khalilov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to R. R. Gataullin.

Additional information

Original Russian Text © R.R. Gataullin, Z.A. Ibatullina, E.S. Meshcheryakova, A.A. Fatykhov, L.M. Khalilov, 2017, published in Zhurnal Organicheskoi Khimii, 2017, Vol. 53, No. 5, pp. 688–698.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Gataullin, R.R., Ibatullina, Z.A., Meshcheryakova, E.S. et al. Atropisomeric N-acyl-N-(cyclopentenylphenyl)glycines in the synthesis of oxazolo[3,4-a]benzoxazocinones. Russ J Org Chem 53, 697–708 (2017). https://doi.org/10.1134/S1070428017050098

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428017050098

Search

Navigation