Synthesis of heterocyclic compounds through palladium-catalyzed C-H cyclization processes.

Chemical & pharmaceutical bulletin (2013-10-04)
Kiyofumi Inamoto
RESUMO

Herein, we describe our development of synthetic methods for heterocyclic compounds based on the palladium-catalyzed carbon-hydrogen bond (C-H) functionalization/intramolecular carbon-heteroatom (nitrogen or sulfur) bond formation process. By this C-H cyclization method, we efficiently prepared various N-heterocycles, including indazoles, indoles, and 2-quinolinones, as well as S-heterocycles such as benzothiazoles and benzo[b]thiophenes. Yields are typically good to high and good functional-group tolerance is observed for each process, thereby indicating that the method provides a novel, highly applicable synthetic route to the abovementioned biologically important heterocyclic frameworks. As an application of this approach, an auto-tandem-type, one-pot process involving the oxidative Heck reaction and subsequent C-H cyclization using cinnamamides and arylboronic acids as starting materials in the presence of a palladium catalyst was also developed for the rapid construction of the 2-quinolinone nucleus.

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Palladium, foil, light tested, 25x25mm, thickness 0.006mm, 99.95%
Palladium, foil, light tested, 25x25mm, thickness 0.025mm, as rolled, 99.95%
Palladium, foil, light tested, 25x25mm, thickness 0.025mm, as rolled, 99.99+%
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Palladium, foil, light tested, 25x25mm, thickness 0.047mm, as rolled, 99.95%
Palladium, foil, light tested, 25x25mm, thickness 0.075mm, as rolled, 99.95%
Palladium, foil, light tested, 50x50mm, thickness 0.025mm, as rolled, 99.95%
Palladium, foil, light tested, 50x50mm, thickness 0.025mm, as rolled, 99.99+%
Palladium, foil, light tested, 50x50mm, thickness 0.03mm, as rolled, 99.95%
Palladium, foil, light tested, 50x50mm, thickness 0.047mm, as rolled, 99.95%
Palladium, foil, light tested, 50x50mm, thickness 0.075mm, as rolled, 99.95%
Palladium, foil, not light tested, 100x100mm, thickness 0.004mm, 99.95%
Palladium, foil, not light tested, 100x100mm, thickness 0.005mm, 99.95%
Palladium, foil, not light tested, 100x100mm, thickness 0.006mm, 99.95%
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