Skip to main content
SpringerLink
Log in

Synthesis of 5-amino-4-hetaryl-2,3-dihydro-1h-3-pyrrolones

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

2-Hetaryl-3-oxo-4-phthalimidobutyronitriles (and pentanonitriles) were obtained with high yields by C-acylation of hetarylacetonitriles with N-phthaloylglycine and α-alanine chlorides respectively under the conditions of base catalysis. Hydrazinolysis of the phthaloyl protection in these compounds leads to the formation of 5-amino-4-hetaryl-2,3-dihydro-1H-3-pyrrolones.

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. A. Trani and E. Bellasio, Farmaco Ed. Sci., 38, 940 (1983).

    CAS  Google Scholar 

  2. C. Yaroslavsky, P. Bracha, and R. Glaser, J. Heterocycl. Chem., 26, 1649 (1989).

    CAS  Google Scholar 

  3. O. M. Z. Howard, J. J. Oppenheim, M. G. Melinda, J. M. Covey, and J. Bigelow, J. Med. Chem., 41, 2184 (1998).

    CAS  Google Scholar 

  4. H.-M. Eggenweiler, R. Jonas, M. Wolf, M. Gassen, and T. Welge, Ger. Patent 19953025; Chem. Abstr., 134, 344596(2001).

    Google Scholar 

  5. M. Tanaka, M. Tsuda, and A. Nakamura, PCT Int. Appl. WO Pat. 9936068; Chem. Abstr., 131, 97597 (1999).

    Google Scholar 

  6. M. K. Ibrahim, Egypt. J. Pharm. Sci., 39, 519 (1998).

    CAS  Google Scholar 

  7. O. Attanasi, S. M. Colombani, L. De Crescentini, R. Giorgi, S. Monti, A. Perrone, F. R. Perrulli, A. R. Renzetti, and S. Santeusanio, Farmaco, 54, 64 (1999).

    CAS  Google Scholar 

  8. M. Tsuda, M. Tanaka, and A. Nakamura, PCT Int. Appl. WO Pat. 9640634; Chem. Abstr., 126, 117863 (1997).

    Google Scholar 

  9. H. Mizukawa, T. Nakamine, and J. Ogasawara, Jpn. Patent 2000347368; Chem. Abstr., 134, 63772 (2001).

    Google Scholar 

  10. N. Yanagihara, Jpn. Patent 2000327657; Chem. Abstr., 134, 18555 (2001).

    Google Scholar 

  11. S. Ikesu, H. Kita, and Y. Kaneko, Jpn. Patent 07128823; Chem. Abstr., 123, 289615 (1995).

    Google Scholar 

  12. C. E. Stephens and J. W. Sowell, J. Heterocycl. Chem., 35, 933 (1998).

    CAS  Google Scholar 

  13. C. E. Stephens and J. W. Sowell, J. Heterocycl. Chem., 33, 1615 (1996).

    CAS  Google Scholar 

  14. M. Yumoto, T. Kawabuchi, K. Sato, and M. Takashima, Jpn. Patent 10316654; Chem. Abstr., 130, 66386 (1998).

    Google Scholar 

  15. K. A. M. El-Bayouki, W. M. Basyouni, H. Hosni, and A. S. El-Deen, J. Chem. Res. (S), 314 (1995).

  16. A. M. Almerico, G. Cirrincione, P. Diana, S. Grimaudo, G. Dattolo, and E. Aiello, J. Heterocycl. Chem., 32, 985(1995).

    CAS  Google Scholar 

  17. A. Gola, E. Samartzi, V. Bardakos, M. Petroliagi, O. Igglessi-Markopoulou, J. Markopoulos, and J. V. Barkley, J. Heterocycl. Chem., 37, 681 (2000).

    CAS  Google Scholar 

  18. K. Gewald and M. Hentschel, J. Prakt. Chem., 318, 663 (1976).

    CAS  Google Scholar 

  19. H. J. Teuber, G. Sobutz, and B. Erkenbrecher, Arch. Pharm. (Weinheim, Ger.), 313, 851 (1980).

    CAS  Google Scholar 

  20. M. Suesse and S. Johne, J. Prakt. Chem., 323, 647 (1981).

    CAS  Google Scholar 

  21. K.-J. Boosen, Helv. Chim. Acta, 60, 1246 (1977).

    Google Scholar 

  22. Y. L. Chen, R. S. Mansbach, S. M. Winter, E. Brooks, J. Collins, M. L. Corman, A. R. Dunaiskis, W. S. Faraci, R. J. Gallaschu, A. Schmidt, and D. W. Schultz, J. Med. Chem., 40, 1749 (1997).

    CAS  Google Scholar 

  23. C. G. Dave and N. D. Desai, J. Heterocycl. Chem., 36, 729 (1999).

    Article  CAS  Google Scholar 

  24. C. G. Dave and R. D. Shah, J. Heterocycl. Chem., 35, 1295 (1998).

    CAS  Google Scholar 

  25. C. N. Hodge, P. E. Aldrich, Z. R. Wasserman, C. H. Fernandez, G. A. Nemeth, A. Arvanitis, R. S. Cheeseman, R. J. Chorvat, E. Ciganek, T. E. Christos, P. J. Gilligan, P. Krenitsky, E. Scholfield, and P. Strucely, J. Med. Chem., 42, 819 (1999).

    CAS  Google Scholar 

  26. V. Levacher, C. Leroy, G. Dupas, J. Bourguignon, and G. Queguiner, Synth. Commun., 24, 2697 (1994).

    CAS  Google Scholar 

  27. M. C. Cesta, R. Curti, L. Nicolini, and M. Mantovanini, PCT Int. Appl. WO 0029411; Chem. Abstr., 132, 349291 (2000).

    Google Scholar 

  28. Yu. M. Volovenko, L. V. Gofman, and F. S. Babichev, Dokl. Akad. Nauk UkrSSR, Ser. B, 621 (1978).

  29. F. S. Babichev, Yu. M. Volovenko, and L. V. Gofman, USSR Inventor’s Certificate 687070; Byull. Izobr., No. 35, 106 (1979).

    Google Scholar 

  30. Yu. M. Volovenko, L. V. Gofman, and F. S. Babichev, Ukr. Khim. Zh., 45, 857 (1979).

    CAS  Google Scholar 

  31. Yu. M. Volovenko, T. V. Shokol, and F. S. Babichev, Ukr. Khim. Zh., 51, 205 (1985).

    CAS  Google Scholar 

  32. Yu. M. Volovenko, T. V. Shokol, A. S. Merkulov, and F. S. Babichev, Ukr. Khim. Zh., 59, 55 (1993).

    CAS  Google Scholar 

  33. A. V. Tverdokhlebov, Yu. M. Volovenko, and T. V. Shokol, Khim. Geterotsikl. Soedin., 50 (1998).

  34. F. S. Babichev and Yu. M. Volovenko, Ukr. Khim. Zh., 43, 711 (1977).

    CAS  Google Scholar 

  35. Yu. M. Volovenko and F. S. Babichev, Khim. Geterotsikl. Soedin., 557 (1977).

  36. E. V. Resnyanskaya, T. V. Shokol, Yu. M. Volovenko, and A. V. Tverdokhlebov, Khim. Geterotsikl. Soedin., 1412 (1999).

  37. Yu. M. Volovenko, T. A. Volovnenko, A. V. Tverdokhlebov, and I. G. Ryabokon’, Zh. Org. Khim., 37, 1389 (2001).

    Google Scholar 

  38. J. Scheiber and H. Reckleben, Berichte, 46, 2412 (1913).

    CAS  Google Scholar 

  39. E. Pfaehler, Berichte, 46, 1702 (1913).

    CAS  Google Scholar 

  40. J. Scheiber, Berichte, 46, 1100 (1913).

    CAS  Google Scholar 

  41. S. Gabriel, Berichte, 46, 1319 (1913).

    CAS  Google Scholar 

  42. O. Igglessi-Markopoulou and C. Sandris, J. Heterocycl. Chem., 19, 883 (1982).

    CAS  Google Scholar 

  43. O. Igglessi-Markopoulou and C. Sandris, J. Heterocycl. Chem., 22, 1599 (1985).

    Article  CAS  Google Scholar 

  44. Yu. M. Volovenko, A. G. Nemazanyi, I. G. Ryabokon’, and F. S. Babichev, Ukr. Khim. Zh., 54, 295 (1988).

    CAS  Google Scholar 

  45. Yu. M. Volovenko, A. V. Tverdokhlebov, and T. A. Volovnenko, Khim. Geterotsikl. Soedin., 952 (2001).

  46. Yu. M. Volovenko, A. V. Tverdokhlebov, A. P. Gorulya, S. V. Shishkina, R. I. Zubatyuk, and O. V. Shishkin, Eur. J. Org. Chem., 663 (2002).

  47. W. Ozegowski and D. Krebs, J. Prakt. Chem., 301, 18 (1965).

    Google Scholar 

  48. K. Saito, S. Kambe, and Y. Nakano, Synthesis, 210 (1983).

  49. Imperial Chemical Industries Ltd., Netherlands Patent Appl. 6614130; Chem. Abstr., 68, 68976 (1968).

    Google Scholar 

  50. C. Mannich and F. L. Hahn, Berichte, 44, 1542 (1911).

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Taras Shevchenko Kiev University, Kiev, Ukraine

    A. V. Tverdokhlebov, A. B. Lyashenko, Yu. M. Volovenko & A. A. Tolmachev

Authors
  1. A. V. Tverdokhlebov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. A. B. Lyashenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Yu. M. Volovenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. A. A. Tolmachev
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1783–1790, December, 2004.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Tverdokhlebov, A.V., Lyashenko, A.B., Volovenko, Y.M. et al. Synthesis of 5-amino-4-hetaryl-2,3-dihydro-1h-3-pyrrolones. Chem Heterocycl Compd 40, 1536–1542 (2004). https://doi.org/10.1007/s10593-005-0095-6

Download citation

  • Received:

  • Revised:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-005-0095-6

Keywords

Search

Navigation