Abstract
2-Benzyl-, 9-benzyl-, and 2,9-dibenzyl-6-methoxy-1,2,3,4-tetrahydro-β-carbolin-1-ones were synthesized. It is shown that 6-methoxy-1,2,3,4-tetrahydro-β-carbolin-1-one and its 2- and 9-monobenzyl-substituted derivatives react with phosphorus oxychloride to give dichlorophosphoryl derivatives in which the dichlorophosphoryl residue enters into the composition of the cation and is bonded to the oxygen in the 1 position or (in the case of the pyrrole-nitrogen-unsubstituted compounds) the nitrogen atom in the 9 position. The possibility of acetylation of the dichlorophosphoryl compounds in the 5 position with acetic anhydride under mild conditions to give high yields of products was observed. The regularities in the mass spectra and PMR spectra of the β-carbolinone derivatives were exposed.
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Literature cited
H. Henecka, R. Lorenz, and H. Timmler, West German Patent No. 1045411 (1958); Chem. Abstr., 55, 5543 (1961).
R. A. Abramovitch and D. Spencer, Adv. Heterocycl. Chem., 3, 117 (1964).
R. G. Glushkov and V. G. Granik, Usp. Khim., 38, 1989 (1969).
R. G. Glushkov, V. A. Volskova, and O. Yu. Magidson, Khim.-Farmats. Zh., No. 9, 25 (1967).
N. N. Suvorov and V. S. Murashova, Med. Prom., No. 1, 6 (1961).
L. Arnold and A. Holý, Coll. Czech. Chem. Commun., 27, 2886 (1962).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1270–1276, September, 1975.
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Yakhontov, L.N., Uritskaya, M.Y., Anisimova, O.S. et al. Reactions of 6-methoxy-1,2,3,4-tetrahydro-β-carbolin-1-ones and their dichlorophosphoryl-substituted derivatives with acetic anhydride. Chem Heterocycl Compd 11, 1107–1112 (1975). https://doi.org/10.1007/BF00471306
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DOI: https://doi.org/10.1007/BF00471306