Abstract
Syntheses of isomeric azolopyridopyrimidines are described. As starting material the corresponding pyridopyrimidines were used. It could be established that in many cases a transformation of a functional group with the purpose to form an annelated five-membered ring proceeded with ring opening at the pyrimidine part. Subsequent ring closure with one carbon synthons gave then the desired tricyclic heterocycles.
Zusammenfassung
Synthesen von isomeren Azolopyridopyrimidinen werden beschrieben. Als Ausgangsverbindungen dienten die entsprechenden Pyridopyrimidine. Es wurde beobachtet, daß in manchen Fällen der Ringschluß unter Beteiligung einer geeigneten funktionellen Gruppe zu gleichzeitiger Ringöffnung des Pyrimidinringes führte. Durch nachfolgende Cyclisierungen konnten die entsprechenden tricyclischen Heterocyclen dargestellt werden.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Kočevar M., Stanovnik B., Tišler M., Heterocycles15, 293 (1981).
Verček B., Leban I., Stanovnik B., Tišler M., J. Org. Chem.44, 1695 (1979).
Verček B., Leban I., Stanovnik B., Tišler M., Heterocycles9, 1327 (1978).
Kočevar M., Verček B., Stanovnik B., Tišler M., Monatsh. Chem.113, 731 (1982).
Kočevar M.,Tišler M.,Stanovnik B., Tetrahedron38 (1982), in print.
Claudi F., Franchetti P., Grifantini M., Martelli S., J. Org. Chem.39, 3508 (1974).
Franchetti P., Grifantini M., J. Heterocyclic Chem.7, 1295 (1970).
Armarego W. L. F., J. Chem. Soc.1962, 4049.
Godefroy L., Queguiner G., Pastour P., J. Heterocyclic Chem.10, 1077 (1973).
Tišler M., Pure & Appl. Chem.52, 1611 (1980).
Godefroy L., Decormeille A., Queguiner G., Pastour P., C. r. Acad. Sci., Ser. C278, 1421 (1974).
Gabriel S., Stelzner R., Chem. Ber.29, 1300 (1896).
Price C. C., Curtin D. Y., J. Amer. Chem. Soc.68, 914 (1946).
Godefroy L., Queguiner G., Pastour P., C. r. Acad. Sci., Ser. C277, 703 (1973).
The synthesis of 4-chloropyrido(3,2-d)pyrimidine (5) is described in the experimental part for compound8.
Gabriel S., Colman J., Chem. Ber.35, 2831 (1902).
Decormeille A.,Queguiner G.,Pastour P., Bull. soc. chim. France1975, 2757.
Robins R. K., Hitching G. H., J. Amer. Chem. Soc.77, 2265 (1955).
2-Amino-3-(tetrazolyl-5′)pyridine was synthesized from 2-amino-3-cyanopyridine and sodium azide in the presence of glacial acetic acid inn-butanol according to the general methods described in the literature20,21.
McManus J. M., Herbst R. H., J. Org. Chem.24, 1462 (1959).
Herbst R. M., Wilson K. R., J. Org. Chem.22, 1142 (1957).
Potts K. T., Brugel E. G., J. Org. Chem.35, 3448 (1970).
Batterham T. J., NMR Spectra of Simple Heterocycles, p. 288. New York: Wiley. 1973.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Petrič, A., Tišler, M. & Stanovnik, B. Syntheses of some azolopyridopyrimidines. Monatsh Chem 114, 615–624 (1983). https://doi.org/10.1007/BF00798617
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF00798617