Solid-phase synthesis of isocoumarins: a traceless halocyclization approach.
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.
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.
Marine
M
Peuchmaur
Vincent
V
Lisowski
Céline
C
Gandreuil
Ludovic T
LT
Maillard
Jean
J
Martinez
Jean-François
JF
Hernandez
D000480:Alkynes / Q000737:chemistry; D001970:Bromobenzoates / Q000737:chemistry; D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D049934:Isocoumarins / Q000138:chemical synthesis*; D008722:Methods
D000480:Alkynes; D001970:Bromobenzoates; D049934:Isocoumarins