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.
Similar content being viewed by others
Literature cited
O. Ya. Belyaeva, V. G. Granik, and R. G. Glushkov, Khim. Geterotsikl. Soedin., No. 6, 798 (1978).
I. Irwin and D. G. Wibberley, Adv. Heterocycl. Chem., 10, 130 (1969).
S. Minami, T. Schono, and I. Matsumoto, Chem. Pharm. Bull., 19, 1426 (1972).
B. S. Hurlbert, R. Ferone, T. A. Heppmann, G. H. Hitchings, M. Barnet, and S. R. Busby, J. Med. Chem., 11, 711 (1968).
G. H. Hitchings and R. K. Robins, US Patent No. 2697710 (1954); Chem. Abstr., 50, 1093 (1956).
G. H. Hitchings and R. K. Robins, US Patent No. 3021332 (1962); Chem. Abstr., 57, 839 (1962).
G. H. Hitchings and R. K. Robins, US Patent No. 2749344 (1956); Chem. Abstr., 51, 1304 (1957).
G. H. Hitchings and K. W. Ledig, US Patent No. 2937284 (1960); Chem. Abstr., 55, 25999 (1961).
R. K. Robins and G. H. Hitchings, J. Am. Chem. Soc., 77, 2256 (1955).
V. Oakes, R. Pascoe, and H. N. Rydon, J. Chem. Soc., No. 4, 1045 (1956).
A. P. Bhaduri and N. M. Khanna, Indian J. Chem., 4, 447 (1966).
British Patent No. 774095; Chem. Abstr., 52, 2097 (1958).
A. Dornow and O. Hahmann, Arch. Pharm. 290, 61 (1957).
J. De Graw and L. Goodmann, Can. J. Chem., 41, 3137 (1963).
B. M. Pyatin and R. G. Glushkov, Khim.-Farm. Zh., No. 9, 17 (1968).
B. Litgoe, A. R. Todd, and A. Topman, J. Chem. Soc., 316 (1944).
R. K. Robins and G. H. Hitchings, J. Am. Chem. Soc., 80, 3449 (1958).
N. B. Marchenko, V. G. Granik, and R. G. Glushkov, USSR Inventor's No. 531358; Byull. Izobr., No. 23, 197 (1977).
N. B. Marchenko, V. G. Granik, and R. G. Glushkov, USSR Inventor's Certificate No. 554675; Byull. Izobr., No. 35, 209 (1977).
J. Gloede, L. Haase, and H. Gross, Ztschr. Chem., 9, 201 (1969).
V. G. Granik, A. M. Zhidkova, and R. G. Glushkov, Usp. Khim., 46, 685 (1977).
A. F. Keremov, Master's Dissertation, S. Ordzhonikidze All-Union Pharmaceutical-Chemistry Institute, Moscow (1970), p. 36.
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).
V. G. Granik, A. M. Zhidkova, T. F. Vlasova, R. G. Glushkov, and Yu. N. Sheinker, Khim. Geterotsikl. Soedin., No. 4, 533 (1974).
A. M. Zhidkova, V. G. Granik, R. G. Glushkov, A. I. Polezhaeva, and M. D. Mashkovskii, Khim.-Farm. Zh., No. 5, 18 (1976).
G. C. Hopkins, J. P. Jonak, H. Tieckelmann, and H. J. Minnemeyer, J. Org. Chem., 31, 3969 (1966).
G. C. Hopkins, J. P. Jonak, H. J. Minnemeyer, and H. Tieckelmann, J. Org. Chem., 32, 4040 (1967).
J. P. Jonak, G. C. Hopkins, H. J. Minnemeyer, and H. Tieckelmann, J. Org. Chem., 35, 2512 (1970).
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).
Beilstein, XXV, p. 276.
Author information
Authors and Affiliations
Additional information
See [1] for communication XXVI.
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1549–1554, November, 1978.
Rights 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
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00509750