Solid-phase synthesis of isocoumarins: a traceless halocyclization approach.

Marine Peuchmaur, Vincent Lisowski, Céline Gandreuil, Ludovic T Maillard, Jean Martinez, Jean-François Hernandez

Institut des Biomolécules Max-Mousseron, UMR 5247, CNRS, Université Montpellier I, UFR des Sciences Pharmaceutiques et Biologiques, 15 Avenue Charles Flahault, 34093 Montpellier Cedex 5, France.

The Journal of organic chemistry 2009 Jun 5

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A straightforward and traceless solid-phase methodology was developed for the synthesis of isocoumarins. This two-step process involves a Sonogashira cross-coupling reaction between polymer-bound 2-bromobenzoates and terminal alkynes, followed by an electrophile-induced halocyclization of the resulting 2-(alk-1-ynyl)benzoates through activation of the triple bond with the subsequent release of the 3-substituted 4-haloisocoumarins. This polymer-bound parallel synthetic approach allowed us to achieve large diversity in good to excellent yields and purities.

Citation

Marine Peuchmaur, Vincent Lisowski, Céline Gandreuil, Ludovic T Maillard, Jean Martinez, Jean-François Hernandez. Solid-phase synthesis of isocoumarins: a traceless halocyclization approach. The Journal of organic chemistry. 2009 Jun 5;74(11):4158-65