Skip to main content
Log in

Acetals of lactams and acid amides

XXVII. New synthesis of pyrido[2,3-d]pyrimidine derivatives

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

7-Dimethylamino-5-hydroxypyrido[2,3-d]pyrimidine and pyrrolo-, pyrido, and azepino [2,3-b]pyrido[2,3-d]pyrimidine derivatives were synthesized by reaction of acetals of amides and lactams with 4-amino-5-carbethoxypyrimidine derivatives and subsequent intramolecular cyclization of the intermediate amidines. The reactions of these compounds with phosphorus oxychloride and their alkylation reactions were studied.

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

Literature cited

  1. O. Ya. Belyaeva, V. G. Granik, and R. G. Glushkov, Khim. Geterotsikl. Soedin., No. 6, 798 (1978).

    Google Scholar 

  2. I. Irwin and D. G. Wibberley, Adv. Heterocycl. Chem., 10, 130 (1969).

    Google Scholar 

  3. S. Minami, T. Schono, and I. Matsumoto, Chem. Pharm. Bull., 19, 1426 (1972).

    Google Scholar 

  4. B. S. Hurlbert, R. Ferone, T. A. Heppmann, G. H. Hitchings, M. Barnet, and S. R. Busby, J. Med. Chem., 11, 711 (1968).

    Google Scholar 

  5. G. H. Hitchings and R. K. Robins, US Patent No. 2697710 (1954); Chem. Abstr., 50, 1093 (1956).

    Google Scholar 

  6. G. H. Hitchings and R. K. Robins, US Patent No. 3021332 (1962); Chem. Abstr., 57, 839 (1962).

    Google Scholar 

  7. G. H. Hitchings and R. K. Robins, US Patent No. 2749344 (1956); Chem. Abstr., 51, 1304 (1957).

    Google Scholar 

  8. G. H. Hitchings and K. W. Ledig, US Patent No. 2937284 (1960); Chem. Abstr., 55, 25999 (1961).

    Google Scholar 

  9. R. K. Robins and G. H. Hitchings, J. Am. Chem. Soc., 77, 2256 (1955).

    Google Scholar 

  10. V. Oakes, R. Pascoe, and H. N. Rydon, J. Chem. Soc., No. 4, 1045 (1956).

    Google Scholar 

  11. A. P. Bhaduri and N. M. Khanna, Indian J. Chem., 4, 447 (1966).

    Google Scholar 

  12. British Patent No. 774095; Chem. Abstr., 52, 2097 (1958).

  13. A. Dornow and O. Hahmann, Arch. Pharm. 290, 61 (1957).

    Google Scholar 

  14. J. De Graw and L. Goodmann, Can. J. Chem., 41, 3137 (1963).

    Google Scholar 

  15. B. M. Pyatin and R. G. Glushkov, Khim.-Farm. Zh., No. 9, 17 (1968).

    Google Scholar 

  16. B. Litgoe, A. R. Todd, and A. Topman, J. Chem. Soc., 316 (1944).

  17. R. K. Robins and G. H. Hitchings, J. Am. Chem. Soc., 80, 3449 (1958).

    Google Scholar 

  18. N. B. Marchenko, V. G. Granik, and R. G. Glushkov, USSR Inventor's No. 531358; Byull. Izobr., No. 23, 197 (1977).

  19. N. B. Marchenko, V. G. Granik, and R. G. Glushkov, USSR Inventor's Certificate No. 554675; Byull. Izobr., No. 35, 209 (1977).

  20. J. Gloede, L. Haase, and H. Gross, Ztschr. Chem., 9, 201 (1969).

    Google Scholar 

  21. V. G. Granik, A. M. Zhidkova, and R. G. Glushkov, Usp. Khim., 46, 685 (1977).

    Google Scholar 

  22. A. F. Keremov, Master's Dissertation, S. Ordzhonikidze All-Union Pharmaceutical-Chemistry Institute, Moscow (1970), p. 36.

    Google Scholar 

  23. A. M. Zhidkova, V. G. Granik, R. G. Glushkov, T. F. Vlasova, O. S. Anisimova, T. A. Gus'kova, and G. N. Pershin, Khim. Geterotsikl. Soedin., No. 5, 670 (1974).

    Google Scholar 

  24. V. G. Granik, A. M. Zhidkova, T. F. Vlasova, R. G. Glushkov, and Yu. N. Sheinker, Khim. Geterotsikl. Soedin., No. 4, 533 (1974).

    Google Scholar 

  25. A. M. Zhidkova, V. G. Granik, R. G. Glushkov, A. I. Polezhaeva, and M. D. Mashkovskii, Khim.-Farm. Zh., No. 5, 18 (1976).

    Google Scholar 

  26. G. C. Hopkins, J. P. Jonak, H. Tieckelmann, and H. J. Minnemeyer, J. Org. Chem., 31, 3969 (1966).

    Google Scholar 

  27. G. C. Hopkins, J. P. Jonak, H. J. Minnemeyer, and H. Tieckelmann, J. Org. Chem., 32, 4040 (1967).

    Google Scholar 

  28. J. P. Jonak, G. C. Hopkins, H. J. Minnemeyer, and H. Tieckelmann, J. Org. Chem., 35, 2512 (1970).

    Google Scholar 

  29. N. B. Marchenko, V. G. Granik, R. G. Glushkov, E. M. Peresleni, A. I. Polezhaeva, and M. D. Mashkovskii, Khim.-Farm. Zh., No. 11, 49 (1976).

    Google Scholar 

  30. Beilstein, XXV, p. 276.

Download references

Author information

Authors and Affiliations

Authors

Additional information

See [1] for communication XXVI.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1549–1554, November, 1978.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Granik, V.G., Marchenko, N.B. & Glushkov, R.G. Acetals of lactams and acid amides. Chem Heterocycl Compd 14, 1261–1266 (1978). https://doi.org/10.1007/BF00509750

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00509750

Keywords

Navigation