Get access

Scandium-Catalyzed Preparation of Cytotoxic 3-Functionalized Quinolin-2-ones: Regioselective Ring Enlargement of Isatins or Imino Isatins

Authors

  • Prof. Dr. Benito Alcaide,

    Corresponding author
    1. Departamento de Química Orgánica I, Facultad de Química, Universidad Complutense de Madrid, 28040 Madrid (Spain), Fax: (+34) 1-3944103
    • Departamento de Química Orgánica I, Facultad de Química, Universidad Complutense de Madrid, 28040 Madrid (Spain), Fax: (+34) 1-3944103
    Search for more papers by this author
  • Dr. Pedro Almendros,

    Corresponding author
    1. Instituto de Química Orgánica General, IQOG, Consejo Superior de Investigaciones Científicas, CSIC, Juan de la Cierva 3, 28006 Madrid (Spain), Fax: (+34) 91-5644853
    • Instituto de Química Orgánica General, IQOG, Consejo Superior de Investigaciones Científicas, CSIC, Juan de la Cierva 3, 28006 Madrid (Spain), Fax: (+34) 91-5644853
    Search for more papers by this author
  • Dr. Cristina Aragoncillo,

    1. Departamento de Química Orgánica I, Facultad de Química, Universidad Complutense de Madrid, 28040 Madrid (Spain), Fax: (+34) 1-3944103
    Search for more papers by this author
  • Dipl.-Chem. Gonzalo Gómez-Campillos,

    1. Departamento de Química Orgánica I, Facultad de Química, Universidad Complutense de Madrid, 28040 Madrid (Spain), Fax: (+34) 1-3944103
    Search for more papers by this author
  • Prof. Dr. Manuel Arnó,

    1. Departamento de Química Orgánica, Universidad de Valencia, C/Dr. Moliner 50, 46100 Burjassot, Valencia (Spain), Fax: (+34)-96-3543880
    Search for more papers by this author
  • Prof. Dr. Luis R. Domingo

    1. Departamento de Química Orgánica, Universidad de Valencia, C/Dr. Moliner 50, 46100 Burjassot, Valencia (Spain), Fax: (+34)-96-3543880
    Search for more papers by this author

Abstract

Trimethylsilyldiazomethane in the presence of catalytic amounts of Sc(OTf)3 smoothly promotes the ring expansion of isatins or imino isatins to efficiently afford 3-functionalized quinolin-2-ones through controlled ring enlargement. Whereas the ring-expansion reaction of azetidine-2,3-diones led to the adduct resulting from migration of the carbonyl group, the ring-expansion reaction of oxindole derivatives gave the adduct resulting from migration of the aryl group. To rationalize the experimental observations, theoretical studies have been performed. Moreover, the biological activity of some of the synthesized heterocycles has been evaluated in four cancer cell lines.

Ancillary