Synthesis of ring-fused oxazolo- and pyrazoloisoquinolinones by a one-pot Pd-catalyzed carboxamidation and aldol-type condensation cascade process.
A three-component cascade process is described for the synthesis of ring-fused oxazolo- and pyrazoloisoquinolinones by a one-pot carboxamidation/aldol-type condensation reaction. The cascade process involves Pd-catalyzed carboxamidation of an aryl halide/active methylene compound with oxazolidinone or pyrazolidinone, and subsequent intramolecular base-catalyzed cyclization/dehydration through an aldol-type condensation process, to give ring-fused oxazolo- and pyrazoloisoquinolinones. This methodology provides an easy one-step approach to these important classes of nitrogen-containing heterocycles and can tolerate a wide array of functional groups, including ester, nitrile, methoxy, and halide.
Chouhan
Gagan
G
Centre for Catalysis Research and Innovation, Department of Chemistry, University of Ottawa, 10 Marie Curie, Ottawa, Ontario K1N 6N5, Canada.
Alper
Howard
H
D000085:Acetates / Q000737:chemistry; D000097:Acetonitriles / Q000737:chemistry; D000577:Amides / Q000737:chemistry*; D002384:Catalysis; D007546:Isoquinolines / Q000138:chemical synthesis* / Q000737:chemistry*; D010080:Oxazoles / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*; D011720:Pyrazoles / Q000737:chemistry*; D013450:Sulfones / Q000737:chemistry
D000085:Acetates; D000097:Acetonitriles; D000577:Amides; D007546:Isoquinolines; D010080:Oxazoles; D011720:Pyrazoles; D013450:Sulfones; D010165:Palladium; C032159:acetonitrile