Abstract
4-Substituted 3, 4-dihydro-Β-carbolines (X–XVI) were obtained by the Beckman rearrangement of oximes of Β-(indolyl-3′)ketones (I–IV, IX) under the action of phosphorus pentachloride in nitrobenzene. 3, 4-Dihydro-Β-carbolines were converted into Β-carbolines (XV–XVII) on heating with Brown's palladium catalyst in ethylene glycol. Oximes containing the aryl group react on treatment with p-toluene sulfochloride in pyridine with the formation of the arilides of Β-(indolyl-3′)propionic acids.
Similar content being viewed by others
References
J. I. De Graw, I. G. Kennedy, and W. A. Skinner, J. Med. Chem., 10, 127, 1967.
J. I. De Graw and W. A. Skinner, Can. J. Chem., 45, 63, 1967.
L. Velluz, G. Muller, and A. Allais, C. r., 247, 1747, 1958.
G. Muller, A. Allais, and L. Velluz, French patent no. 1344152, 1963; RZhkh, 1965, 14H235.
French patent, no. 1369323, 1366730, 1369956, 1964, RZhKh, 1H191, 193, 194, 1966.
P. A. Vember, I. V. Terent'eva, and G. V. Lazur'evskii, KhPS [Chemistry of Natural Compounds], 249, 1967.
P. A. Vember and I. V. Terent'eva, KhPS [Chemistry of Natural Compounds], 98, 1968.
C. K. Bradsher and E. F. Litzinger, J. Org. Chem., 29, 3584, 1964.
A. A. Semenov, I. V. Terent'eva, and E. P. Styngach, KhGS [Chemistry of Heterocyclic Compounds], collection 1, 38, 1967.
A. A. Semenov, KhGS [Chemistry of Heterocyclic Compounds], collection 1, 44, 1967.
A. A. Semenov, E. P. Styngach, and G. M. Kuperman, KhGS [Chemistry of Natural Compounds], 878, 1968.
J. Szmuszkowicz, J. Am. Chem. Soc., 79, 2819, 1957.
R. T. Conley and R. E. Novak, J. Org. Chem., 27, 3196, 1962.
L. G. Donaruma and V. Z. Khel'dt, Org. reaktsii, 11, 14, Moscow, 1965.
E. Wenkert and D. K. Rovchaundhuri, J. Am. Chem. Soc., 80, 1613, 1958.
H. C. Brown, Tetrah., 22, Suppl. 8, 149, 1966.
L. E. Weller and T. L. Rebstock, J. Am. Chem. Soc., 74, 2690, 1952.
K. I. Kuchkova and A. A. Semenov, KhGS [Chemistry of Nutural Compounds], 1136, 1967.
Author information
Authors and Affiliations
Additional information
For preliminary report, see [18].
Rights and permissions
About this article
Cite this article
Kuchkova, K.I., Semenov, A.A. & Terent'eva, I.V. Carbolines. Chem Heterocycl Compd 6, 182–186 (1970). https://doi.org/10.1007/BF00474993
Issue Date:
DOI: https://doi.org/10.1007/BF00474993