Summary
5-Phenyl-barbituric acids (1) can be cyclized to Benzofuro[2,3-d]pyrimidines (3) either directly by cyclodehydrogenation with palladium-charcoal or via oxidation to 3-hydroxy-3-phenylbarbituric acids (2) and subsequent cyclodehydratation by treatment with strong acids.
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Murray R. D. H., Mendez J., Brown S. A. (1982) In: The Natural Coumarins. Wiley, Chichester, p. 320
Muccu Y. R., Kirkland J. L., Sancel G. M. (1981) Trends in Pharmacol. Sci.3: 98
Stadlbauer W., Schmut O., Kappe T. (1980) Monatsh. Chem.111: 1005;
Kappe T., Schmidt H. (1972) Org. Prep. Proc. Int.4: 233; Kappe T., Brandner A. (1974) Z. Naturforsch.29 b: 292
Kappe T., Brandner A., Stadlbauer W. (1987) Monatsh. Chem.118: 1177
Stadlbauer W., Kappe T. (1975) Z. Naturforsch.30 b: 139
Ames D. E., Bull D. (1982) Tetrahedron38: 383; Ames D. E., Opalko A. (1984) Tetrahedron40: 1919
Jovanovic M. V., Biehl E. R. (1986) Heterocycles24: 3129; De Mester P., Jovanovic M. V., Chu S. S. C., Biehl E. R. (1986) J. Heterocycl. Chem.23: 337; Tate J. V., Trinnermann W. N., Jurevics V., Jeskey H., Biehl E. R. (1986) J. Heterocycl. Chem.23: 9; Jovanovic M. V., Biehl E. R. (1987) J. Heterocycl. Chem.24: 191
Youssefyeh R. D., Weisz M. (1973) Tetrahedron Lett.14: 4317
Pfleiderer W., Deiss H. (1968) Israel. J. Chem.1968: 603
Youssefyeh R. D., Weisz M. (1974) J. Am. Chem. Soc.96: 315
Stadlbauer W., Kappe T. (1985) Monatsh. Chem.116: 1995; Stadlbauer W., Kappe T. (1982) Z. Naturforsch.37 b: 1196
Lapachev V., Stadlbauer W., Kappe T. (1988) Monatsh. Chem.119: 97
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Stadlbauer, W. Synthesen von Benzofuro[2,3-d]pyrimidin-2,4-dionen. Monatsh Chem 120, 77–80 (1989). https://doi.org/10.1007/BF00809652
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DOI: https://doi.org/10.1007/BF00809652