Investigations into the mechanism of lactamization of lactones yielding in a novel route to biologically active tryptamine derivatives |
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Authors: | Michael Decker |
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Institution: | Lehrstuhl für Pharmazeutische/Medizinische Chemie, Institut für Pharmazie, Friedrich-Schiller-Universität Jena, Philosophenweg 14, D-07743 Jena, Germany |
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Abstract: | The mechanism of lactamization of corresponding lactones was investigated by means of gas chromatography and synthesis of possible intermediates as references. Lactones react with amines via the amino acid with subsequent elimination of water to the corresponding lactams. In the first step, also hydroxyamides are in equilibrium with the lactones and amines, respectively, which are not able to form the amide though. This mechanism opens a new approach for the synthesis of Nβ-disubstituted tryptamines. |
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Keywords: | Lactamization Lactones Amino acids Hydroxyamides Tryptamines Hallocinogens |
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