Skip to main content
SpringerLink
Log in

Simple and efficient synthesis of new O,O-diethyl phosphorothioates

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

Abstract

A simple and highly effective method was developed for the synthesis of new O,O-diethyl phosphorothioates from O,O-diethyl phosphorochloridothioate and 2-chloroquinolin-3-ylmethanol derivatives in the presence of sodium hydroxide.

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. Heterocyclic Compounds, Elderfield, R., Ed., New York: Wiley, 1952, vol. 4, p. 1; Meth-Cohn, O. and Narine, B., Tetrahedron Lett., 1978, vol. 19, p. 2045; Ali, M.M., Tasneem, Rajanna, K.C., and Sai Prakash, P.K., Synlett, 2001, no. 2, p. 251 (see also references cited therein).

    Google Scholar 

  2. Patel, H.V., Vyas, K.V., and Fernandes, P.S., Indian J. Chem., Sect. B, 1990, vol. 29, p. 836.

    Google Scholar 

  3. Sukhova, N.M., Lidak, M., Zidermane, A., Pelevina, I.S., and Voronina, S.S., Khim.-Farm. Zh., 1989, vol. 23, p. 1226.

    CAS  Google Scholar 

  4. Dillard, R.D., Pavey, D.E., and Benslay, D.N., J. Med. Chem., 1973, vol. 16, p. 251.

    Article  CAS  Google Scholar 

  5. Craig, J.C. and Pearson, P.E., J. Med. Chem., 1971, vol. 14, p. 1221.

    Article  CAS  Google Scholar 

  6. Meth-Cohn, O., Heterocycles, 1993, vol. 35, p. 539 (see also references cited therein); Rajendran, S.P., Manonmani, M., and Vijaya-Lakshmi, S., Org. Prep. Proced. Int., 1994, vol. 26, p. 383.

    Article  CAS  Google Scholar 

  7. Handbook of Organophosphorus Chemistry, Engel, R., Ed., New York: Marcel Dekker, 1992.

    Google Scholar 

  8. Hong, S.-B., Mullins, L.S., Shim, H., Raushrl, F.M., Biochemistry, 1997, vol. 36, p. 9022; Berggren, M.M., Burns, L.A., Abraham, R.T., and Powis, G., Cancer Res., 1993, vol. 53, p. 1862; Cao, X.D., Moran, E.J., Siev, D., Lo, A., Ohashi, C., and Mjalli, A.M.M., Bioorg. Med. Chem. Lett., 1995, vol. 5, p. 2953.

    Article  CAS  Google Scholar 

  9. Widlanski, T.S., Myers, J.K., Stec, B., Holtz, K.M., and Kantrowitz, E.R., Chem. Biol., 1997, vol. 4, p. 489; Stowell, J.K., Widlanski, T.S., Kutateladze, T.G., and Raines, R.T., J. Org. Chem., 1995, vol. 60, p. 6930.

    Article  CAS  Google Scholar 

  10. Maurer, F., Riebel, H.J., Hammann, L., Behrenz, W., and Homeyer, B., Ger. Offen. no. 2 533 601, 1977.

  11. Molodykh, Z.V., Aleksandrova, I.A., Belyalov, R.U., Gazizov, T.K., and Reznik, V.S., Khim.-Farm. Zh., 1990, vol. 24, p. 136.

    CAS  Google Scholar 

  12. Drake, G.L. and Calamari, T.A., The Role of Phosphonates in Living Systems, Hilderbrand, R.L., Ed., Boca Raton: CRC, 1983, chap. 7.

    Google Scholar 

  13. Fields, S.C., Tetrahedron, 1999, vol. 55, p. 12 237; Yokomatsu, T., Yoshida, Y., and Shibuya, S., J. Org. Chem., 1994, vol. 59, p. 7930.

    Article  CAS  Google Scholar 

  14. Kafarski, P. and Lejczak, B., Phosphorus, Sulfur, Silicon Relat. Elem., 1991, vol. 63, p. 193.

    Article  CAS  Google Scholar 

  15. Allen, M.C., Fuhrer, W., Tuck, B., Wade, R., and Wood, J.M., J. Med. Chem., 1989, vol. 32, p. 1652; Giannousis, P.P. and Bartlett, P.A., J. Med. Chem., 1987, vol. 30, p. 1603.

    Article  CAS  Google Scholar 

  16. Atherton, F.R., Hassal, C.H., and Lambert, R.W., J. Med. Chem., 1986, vol. 29, p. 29; Baylis, E.K., Campbell, C.D., and Dingwall, J.G., J. Chem. Soc., Perkin Trans. 1, 1984, p. 2845.

    Article  CAS  Google Scholar 

  17. Engel, R., Chem. Rev., 1977, vol. 77, p. 349.

    Article  CAS  Google Scholar 

  18. Markowska, A., Młotkowska, B., Olejnik, J., and Sażała, M., Justus Liebigs Ann. Chem., 1993, p. 1327.

  19. Uhlman, E. and Peyman, A., Chem. Rev., 1990, vol. 90, p. 543; Stein, C.A. and Cheng, Y.C., Science, 1993, vol. 261, p. 1004; Elzagheid, M.L., Mattila, K., Oivanen, M., Jones, B.C.N.M., Cosstick, R., and Lönnberg, H., Eur. J. Org. Chem., 2000, p. 1987.

    Article  Google Scholar 

  20. Yoshida, M., Maeda, T., and Sugiyama, H., JPN Patent Appl. no. 42-1541, 1967; Chem. Abstr., 1967, vol. 66, p. 115 455.

  21. Folkin, A.V., Kolomiets, A.F., and Iznoskova, M.G., Izv. Akad. Nauk. SSSR, Ser. Khim., 1974, p. 2837; Schrader, G., US Patent no. 2 597 534, 1952.

  22. Michalski, J., Modro, T., and Wieczorkowski, J., J. Chem. Soc., 1960, p. 1665.

  23. Michalski, J. and Wasiak, J., J. Chem. Soc., 1962, p. 5056; Michalski, J., Wasiak, J., Wieczorkowski, J., and Pliszka, B., Roczn. Chem., 1959, vol. 33, p. 247; Harvey, R.G., Jacobson, H.I., and Jensen, E.V., J. Am. Chem. Soc., 1963, vol. 85, p. 1618.

  24. Sato, Z., Takagi, K., Imamiya, Y., Shimizu, F., and Kusano, S., Ger. Offen. no. 2 601 532, 1976; Schrader, G. and Lorenz, W., US Patent no. 2 862 017, 1958.

  25. Sallmann, R., Swiss Patent no. 324 980, 1957.

  26. Watanabe, Y., Inoue, S., Yamamoto, T., and Ozaki, S., Synthesis, 1995, p. 1243.

  27. Mane, A.S., Chavan, V.P., Karale, B.K., Hangarge, R.V., Gaikwad, M.S., and Shingare, M.S., Synth. Commun., 2002, vol. 32, p. 2633; Chavan, V.P., Mane, A.S., and Shingare, M.S., Indian J. Chem., Sect. B, 2001, vol. 40, p. 339; Pokalwar, R.U., Hangarge, R.V., Maske, P.V., and Shingare, M.S., Arkivoc, 2006, part (xi), p. 196.

    Article  CAS  Google Scholar 

  28. Meth-Cohn, O., Narine, B., and Tarnowski, B., J. Chem. Soc., Perkin Trans. 1, 1981, p. 1520.

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University, Aurangabad, 431004 (M.H.), India

    R. U. Pokalwar, R. V. Hangarge, A. H. Kategaonkar & M. S. Shingare

Authors
  1. R. U. Pokalwar
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. R. V. Hangarge
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. H. Kategaonkar
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. M. S. Shingare
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to R. U. Pokalwar.

Additional information

Published in Russian in Zhurnal Organicheskoi Khimii, 2009, vol. 45, No. 3, pp. 440–443.

The text was submitted by the authors in English.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Pokalwar, R.U., Hangarge, R.V., Kategaonkar, A.H. et al. Simple and efficient synthesis of new O,O-diethyl phosphorothioates. Russ J Org Chem 45, 430–433 (2009). https://doi.org/10.1134/S1070428009030142

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428009030142

Keywords

Search

Navigation