Abstract
Aliphatic-aromatic sulfonamide analogs of melatonin were obtained by acylation of 5-methoxytryptamine with 4-(N,N-diethylsulfonamidoaryl)pentanoyl chlorides. It is shown that cyclization of the indicated amides under the conditions of the Bischler-Napieralski reaction leads to the formation of 3,4-dihydro-β-carbolines in good yields without involvement of the sulfonamido group. The corresponding 1,2,3,4-tetrahydro-β-carbolines were obtained by reduction of the latter with sodium metal in absolute methanol and were characterized.
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M. Protiva, L. Lilek, E. Hachova, L. Novak, Z. Vejdelek, and E. Adlerova, Chem. Listy, No. 5, 1915 (1957).
D. R. Lagidze and L. Ya. Talakvadze, Soobshch. Akad. Nauk Gruz. SSR, 72, 97 (1973).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1648–1650, December, 1977.
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Lagidze, D.R., Talakvadze, L.Y. & Lagidze, R.M. Synthesis of some new aliphatic-aromatic sulfonamide analogs of melatonin, 3,4-dihydro-β-carboline, and 1,2,3,4-tetrahydro-β-carboline. Chem Heterocycl Compd 13, 1316–1318 (1977). https://doi.org/10.1007/BF00469893
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DOI: https://doi.org/10.1007/BF00469893