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  • An Alternative Synthesis Of 1,2,3,4-tetrahydro-9h-pyrido-[3,4-b]-indole [uma Síntese Alternativa Para O (± )-1,2,3,4-tetraidro-{9h-pirido-[3,4-b]}-indol]
    2015
    Co-Authors: De Oliveira A.j.b., Koike L.
    Abstract:

    The 1,2,3,4-tetrahydro-9H-pyrido-[3,4-b]-indole, a compound with tranquillizing properties, was prepared in 16% overall yield from the 3-indole-acetaldehyde and tryptamine by applying the classical Pictet-Spengler condensation. Physical and spectroscopic data for such compound are presented.393259264Cox, E.D., Cook, J.M., The Pictet-Spengler condensation: A new direction for an old reaction (1995) Chem. Rev., 95 (6), pp. 1797-1842Cordell, G.A., (1981) Introduction to Alkaloids: A Biogenetic Approach, p. 1055. , New York: WilleyGaignault, Vacher, J., Frechet, D., [9H]-pyrido-[3,4-b]-indoles. United States Patent n. 4,0005,206, Jan. 25, 1977Lukáts, P.A., Károlyházy, J.M., Szabó, L., Podány, B., First direct and detailed stereochemical analysis of strictosidine (1997) J. Nat. Prod., 60 (2), pp. 69-75Massiot, G., Boumendji, A., Nuzillard, J.M., Une synthése facile du tryptophaldéhyde. Syntése et détermination de structure de le murraycarine (1990) Bull. Soc. Chem. Fr., 127, pp. 645-647. , ParisMoffat, J.G., Pfitzner, K.E., Sulfoxide-carbodiimidé reactions. II Scope of oxidation reactions (1965) J. Am. Chem. Soc., 87, pp. 5670-5678. , ColumbusRaman, A.U., Basha, A., (1983) BioSynthesis of Indole Alkaloids, pp. 45-93. , Oxford: Clarendon PressRobert, G.M.T., Ahond, A., Poupat, C., Potier, P., Jollês, C., Jousselin, A., Aspidosperma de Guyane: Alcaloïdes de Aspidosperma marcgravianum (1983) J. Nat. Prod., 46 (5), pp. 694-707. , ColumbusWhaley, W.M., Govindachari, T.R., The Pictet-Spengler Synthesis of tetrahydroisoquinolines and related compounds (1951) Organic Reactions, 6, p. 151. , Adams, R., ed. New York: Wile