Abstract
A new synthesis of the indole system has been achieved by chclodehydrogenation of amino phenylmalonate heterocycles. Thus, the 4-amino coumarins1 a,b or the 4-amino-2-quinolones1 c–g are converted to the indoles2 with palladium on charcoal in boiling diphenyl ether. The reaction of the aminocompounds1 with diphenyl carbonate yields the fused polycyclic isoquinolones4.
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Literatur
Saxton J. E., in: The Alkaloids (Manske, Hrsg.), Bd.VII, S. 4 ff. (1960); Bd.VII, S. 1 ff. (1965). New York-London: Academic Press;Hesse M., Alkaloidchemie, 1. Aufl., S. 20. Stuttgart: G. Thieme. 1978.
Winterfeldt E., Altmann H. J., Angew. Chem.80, 486 (1968); Intern. Ed. Engl.7, 466 (1968).
Bergman J., Carlsson R., Sjöberg B., J. Heterocycl. Chem.14, 1123 (1977).
Dave V., Warnhoff E. W., Tetrahedron31, 1255 (1975).
Bourdais J., Lorre A., J. Heterocycl. Chem.12, 1111 (1975).
Braunholtz J. T.,Mann F. G., J. Chem. Soc.1955, 381.
De Diesbach H., Gross J., Tschannen W., Helv. Chim. Acta34, 1050 (1951).
Walser A., Silverman G., Flynn T., Fryer R. I., J. Heterocycl. Chem.12, 351 (1975).
Trkovnik M., Djudjic R., Tabakovic I., Kules M., Org. Prep. Proc. Int.14, 21 (1982);Osman A. M., Hammam A. S., Khalil Z. H., Yanni A. S., Ind. J. Chem.21 B, 325 (1982);Dagher C., Hanna R., Terentiev P. B., Boundel Y. G., Kost A. N., Maksimov B. I., J. Heterocycl. Chem.19, 645 (1982).
Kappe Th., Schmidt H., Org. Prep. Proc. Int.4, 233 (1972).
Kappe Th., Brandner A., Z. Naturforsch.29 b, 292 (1974).
Stadlbauer W., Kappe Th., Z. Naturforsch.30 b, 139 (1975).
Ahluwalia V. K., Prakash V., Rani N., Ind. J. Chem.16 B, 372 (1978).
Stadlbauer W., Schmut O., Kappe Th., Monatsh. Chem.111, 1005 (1980).
Stadlbauer W., Kappe Th., Monatsh. Chem.113, 751 (1982).
Curd F. H. S.,Raison C. G.,Rose F. L., J. Chem. Soc.1947, 899.
Stadlbauer W.,Kappe Th., Synthesis1981, 833.
Baumgarten P., Riedel M., Ber. dtsch. chem. Ges.75, 984 (1942).
Jacobs R. T., Wright A. D., Smith F. X., J. Org. Chem.47, 3769 (1982).
Stadlbauer W., Ghobrial N., Kappe Th., Z. Naturforsch.35 b, 892 (1980).
Stadlbauer W., Kappe Th., Monatsh. Chem.109, 1485 (1978).
Kessar S. V., Pahwa P. S., Pawanjit S. P., Gupta Y. P., Ind. J. Chem.16 B, 92 (1978).
Chatterjea J. N., Banerjee B. K., Prasad N., J. Ind. Chem. Soc.42, 283 (1965).
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Stadlbauer, W., Kappe, T. Synthese von Indolen und Isochinolonen aus Phenylmalonylheterocyclen. Monatsh Chem 115, 467–475 (1984). https://doi.org/10.1007/BF00810008
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DOI: https://doi.org/10.1007/BF00810008