Summary
1-Amino-5-benzoyl-4-phenyl-1H-pyrimidine derivatives1 add arylisocyanates2 to give the N,N′-disubsituted ureas3 which can be cyclized by use of oxalyl dichloride to the imidazolyl-pyrimidinones(thiones)4. In addition,1 is transferred into the desaminated pyrimidines6 either by diazotation reaction or by thermolysis of the parental functionalized pyrimidine derivatives7.
Zusammenfassung
1-Amino-5-benzoyl-4-phenyl-1H-pyrimidin-2-one(thione)1 addieren Arylisocyanate2 in guten Ausbeuten (60–95%) zu den Pyrimidinylharnstoff-Derivaten3, die ihrerseits mit Oxalylchlorid zu den Imidazolyl-pyrimidinen4 cyclisierbar sind. Versuche, die Amino-Verbindungen1 zu diazotieren, führen unter N2-Eliminierung zu den desaminierten Pyrimidinen6, die andererseits auch durch einfache Thermolyse der Methylenamino-pyrimidine7 entstehen.
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References
Part 29: Altural B., Akcamur Y., Saripinar E., Yildirim I., Kollenz G. (1989) Monatsh. Chem.120: 1015
Akcamur Y., Altural B., Saripinar E., Kollenz G., Kappe O., Peters K., Peters E. M., von Schnering H. G. (1988) J. Heterocycl. Chem.25: 1419
Saunders J. H., Slocombe R. J. (1948) Chem. Rev.43: 203;
Arnold R. G., Nelson J. A., Verbanc J. J. (1957) Chem. Rev.57: 47;
Abdel-Megeed M. F., Tenion A. (1988) Rev. Roum. Chim.33: 981
Cheng C. C. (1969) Prog. Med. Chem.: 67;
Kleemann A., Engel J. (1982) Pharmazeut. Wirkstoffe, 2. Aufl. Thieme, Stuttgart New York, pp. 25, 225, 375, 478, 641
Lomis T. J., Suida J. F., Shepherd R. E. (1988) J. Chem. Soc. Chem. Comm.: 290
The Aldrich Library of IR-Spectra, Ed. III (Pouchert C. J., ed.) (1981) Aldrich Chem. Comp. Inc., pp. 1087–1088
Katritzky A. R., Ambler A. P. (1963) In: Katritzky A. R. (ed.) Physical Methods in Heterocyclic Chemistry, Vol. II. Academic Press, New York, pp. 165 ff
Liebscher J., Hassoun A., Fabian J. (1989) Monatsh. Chem.120: 749
Ulrich H., Saying A. A. R. (1966) Angew. Chem.78: 761; (1966) Angew. Chem. Int. Ed. Engl.5: 704
Ulrich H., Saying A. A. R. (1965) J. Org. Chem.30: 2781
Stoffel P. J. (1964) J. Org. Chem.29: 2794;
Biltz H., Topp E. (1913) Ber. Dtsch. Chem. Ges.47: 1387
Sheehan J. C., Corey E. J. (1952) J. Am. Chem. Soc.74: 360;
Speciale A. J., Smith L. R. (1963) J. Org. Chem.28: 1805;
Sasaki T., Eguchi S., Toru T. (1968) Tetrahedron Lett.38: 4135
Curtius T., Darapsky A., Müller E. (1907) Ber. Dtsch. Chem. Ges.40: 815;
Beyer H., Wolter G. (1956) Chem. Ber.89: 1657;
Beyer H., Lässwig W., Bulka E. (1954) Chem. Ber.87: 1386;
Ibrahim Y. A., Eid M. M., Abdel-Hady S. A. (1980) J. Heterocycl. Chem.17: 1733;
Dornow A., Menzel H., Marx P. (1964) Chem. Ber.97: 2173
Bopat J. B., Blade R. J., Boulton A. J., Epsztajn J., Katritzky A. R., Lewis J., Molina-Buendia P., Pai-Lin Nie, Ramsden C. A. (1976) Tetrahedron Lett.31: 2691;
Fahmy A. F. M., Fayed M. S., Ibrahim Y. A. (1978) Chem. Ind. (London): 13
Hoffmann H. M. R. (1969) Angew. Chem.81: 612; (1969) Angew. Chem. Int. Ed. Engl.8: 571
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Dedicated to o. Univ. Prof. Dr. F. Sauter on the occasion of his 60th birthday
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Altural, B., Kollenz, G. Reactions of cyclic oxalyl compounds, Part 30: Some reactions with N-amino-pyrimidine derivatives. Monatsh Chem 121, 677–682 (1990). https://doi.org/10.1007/BF00809772
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DOI: https://doi.org/10.1007/BF00809772