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Prof. Dr. Benito Alcaide, Dr. Pedro Almendros, Dr. Cristina Aragoncillo, Dipl.-Chem. Gonzalo Gómez-Campillos, Prof. Dr. Manuel Arnó and Prof. Dr. Luis R. Domingo Scandium-Catalyzed Preparation of Cytotoxic 3-Functionalized Quinolin-2-ones: Regioselective Ring Enlargement of Isatins or Imino Isatins ChemPlusChem 77

Version of Record online: 23 MAY 2012 | DOI: 10.1002/cplu.201200090

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Ring expansion of isatins: A variety of 3-hydroxy (or 3-amino) quinolin-2-one derivatives have been prepared through scandium-catalyzed controlled ring expansion of isatins or imino isatins by reaction with trimethylsilyldiazomethane (see scheme). Moreover, density functional calculations and cytotoxic studies were performed to obtain insights into both the reaction mechanism and the biological activity, respectively.

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