Skip to main content
Log in

Synthesis of Chiral 3,4-Dihydropyrimidin-2(1H)-one Derivatives and Their Stereoselective Chlorination with Chlorine Dioxide

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

Abstract

Optically active derivatives of 3,4-dihydropyrimidin-2(1H)-one have been synthesized on the basis of myrtenal and methyl 2,3-O-isopropylidene-α-L-erythro-pentodialdo-1,4-furanoside in 45 and 50% yields, respectively, and subjected to stereoselective chlorination with chlorine dioxide, which afforded a series of mono-, di-, and trichloro derivatives in up to 98% yield.

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. Kaan, H.Y.K., Ulaganathan, V., Rath, O., Prokopcov, H., Dallinger, D., Kappe, C.O., and Kozielski, F., J. Med. Chem., 2010, vol. 53, p. 5676.

    Article  CAS  PubMed  Google Scholar 

  2. Kappe, C.O., Tetrahedron, 1993, vol. 49, p. 6937.

    Article  CAS  Google Scholar 

  3. Kappe, C.O., Acc. Chem. Res., 2000, vol. 33, p.879.

    Article  CAS  PubMed  Google Scholar 

  4. Kappe, C.O., Eur. J. Med. Chem., 2000, vol. 35, p. 1043.

    Article  CAS  PubMed  Google Scholar 

  5. Sandhu, S. and Sandhu, J.S., Arkivoc, 2012, part (i), p.66.

    Google Scholar 

  6. Maliga, Z., Kapoor, T.M., and Mitchison, T.J., Chem. Biol., 2002, vol. 9, no. 9, p.989.

    Article  CAS  PubMed  Google Scholar 

  7. Barrow, J.C., Nantermet, P.G., Selnick, H.G., Glass, K.L., Rittle, K.E., Gilbert, K.F., Steele, T.G., Homnick, C.F., Freidinger, R.M., Ransom, R.W., Kling, P., Reiss, D., Broten, T.P., Schorn, T.W., Chang, R.S., O’Malley, S.S., Olah, T.V., Ellis, J.D., Barrish, A., Kassahun, K., Leppert, P., Nagarathnam, D., and Forray, C., J. Med. Chem., 2000, vol. 43, p. 2703.

    Article  CAS  PubMed  Google Scholar 

  8. Goldstein, C., Schroeder, J.C., Fortin, J.P., Goss, J.M., Schaus, S.E., Beinborn, M., and Kopin, A.S., J. Pharmacol. Exp. Ther., 2010, vol. 335, p.799.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  9. Matache, M., Dobrota, C., Bogdan, N.D., Dumitru, I., Ruta, L.L., Paraschivescu, C.C., Farcasanu, I.C., Baciu, I., and Funeriu, D.P., Tetrahedron, 2009, vol. 65, p. 5949.

    Article  CAS  Google Scholar 

  10. Da, Y.X., Zhang, Z., and Quan, Z.J., Chin. Chem. Lett., 2011, vol. 22, p.679.

    Article  CAS  Google Scholar 

  11. Akhaja, T.N. and Raval, J.P., Chin. Chem. Lett., 2012, vol. 23, p.446.

    Article  CAS  Google Scholar 

  12. Rostamnia, S. and Lamei, K., Chin. Chem. Lett., 2012, vol. 23, p.930.

    Article  CAS  Google Scholar 

  13. Heravi, M.M., Karimi, N., Hamidi, H., and Oskooie, H.A., Chin. Chem. Lett., 2013, vol. 24, p.143.

    Article  CAS  Google Scholar 

  14. Kiyani, H. and Ghiasi, M., Res. Chem. Intermed., 2015, vol. 41, p. 5177.

    Article  CAS  Google Scholar 

  15. Lopez Aparicio, F.J., Lopez Sastre, J.A., Molina Molina, J., and Romero-Avila Garcia, M.C., An. Quim. Ser. C, 1981, vol. 77, p.348.

    CAS  Google Scholar 

  16. Valpuestra Fernandez, M., Lopez Herrera, F.J., and Lupron Cobos, T., Heterocycles, 1986, vol. 24, p.679.

    Article  Google Scholar 

  17. Valpuestra Fernandez, M., Lopez Herrera, F.J., and Lupron Cobos, T., Heterocycles, 1988, vol. 27, p. 2133.

    Article  Google Scholar 

  18. Zhu, Y.-W. and Shi, Y.-X., Catal. Lett., 2016, vol. 146, p.570.

    Article  CAS  Google Scholar 

  19. Zigeuner, G., Hamberger, H., Blaschke, H., and Sterk, H., Monatsh. Chem., 1966, vol. 97, p. 1408.

    Article  CAS  Google Scholar 

  20. Khanina, E.L., Liepin’sh, E.E., Mutsenietse, D.Kh., and Dubur, G.Ya., Chem. Heterocycl. Compd., 1987, vol. 23, p.554.

    Article  Google Scholar 

  21. Tale, N.P., Shelke, A.V., Bhong, B.Y., and Karade, N.N., Monatsh. Chem., 2013, vol. 144, p.981.

    Article  CAS  Google Scholar 

  22. Rav-Acha, C. and Chosshen, E., Environ. Sci. Technol., 1987, vol. 21, p. 1069.

    Article  CAS  Google Scholar 

  23. Tumanova, T.A. and Flis, I.E., Fiziko-khimicheskie osnovy otbelki (Physicochemical Basis of Bleaching), Moscow: Lesnaya Promyshlennost’, 1972, p.236.

    Google Scholar 

  24. Sedaghat, S., Afr. J. Pure Appl. Chem., 2013, vol. 7, no. 1, article no. DF637A83390.

    Google Scholar 

  25. Tronchet, J.M.J., Gentile, B., Bonenfant, A.P., and Martin, O.R., Helv. Chim. Acta, 1979, vol. 62, p.696.

    Article  CAS  Google Scholar 

  26. Ramos, L.M., Ponce de Leon y Tobio, A.Y., Santos, M.R., Oliveira, H.C.B., Gomes, A.F., Gozzo, F.C., Oliveira, A.L., and Neto, B.A.D., J. Org. Chem., 2012, vol. 77, p. 10 184.

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to E. S. Izmest’ev.

Additional information

Original Russian Text © E.S. Izmest’ev, S.V. Pestova, S.A. Rubtsova, A.V. Kutchin, 2018, published in Zhurnal Organicheskoi Khimii, 2018, Vol. 54, No. 9, pp. 1380–1385.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Izmest’ev, E.S., Pestova, S.V., Rubtsova, S.A. et al. Synthesis of Chiral 3,4-Dihydropyrimidin-2(1H)-one Derivatives and Their Stereoselective Chlorination with Chlorine Dioxide. Russ J Org Chem 54, 1395–1401 (2018). https://doi.org/10.1134/S107042801809021X

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S107042801809021X

Navigation