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Studies on the Regioselectivity of the Cyclization of Tryptophanol-Derived Oxazolopiperidone Lactams

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Cyclization of the lactam carbonyl on the indole ring in tryptophanol-derived oxazolopiperidone lactams 2 and 6, under the classical POCl3-promoted Bischler-Napieralski conditions and under neutral conditions via the corresponding thiolactam, has been studied. Whereas tricyclic lactam 2 only leads to products coming from an α-amidoalkylation process, bicyclic lactam 6 undergoes cyclization on the lactam carbonyl, leading to the expected indolo[2,3-a]quinolizidine derivatives.

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AMAT TUSÓN, Mercedes, et al. Studies on the Regioselectivity of the Cyclization of Tryptophanol-Derived Oxazolopiperidone Lactams. European Journal of Organic Chemistry. 2013. Vol. 1246-1252. ISSN 1434-193X. [consulted: 28 of June of 2026]. Available at: https://hdl.handle.net/2445/171749

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