Isoquinolone Synthesis with Palladium Nanoparticles

Isoquinolone Synthesis with Palladium Nanoparticles


N-heterocycles are important building blocks in medicinal chemistry. Isoquinolone (derivative pictured) is an N-heterocyclic scaffold present in many alkaloids and biologically active molecules. The metal-catalyzed cyclization of aromatic amides and alkynes is one protocol for the synthesis of isoquinolone derivatives.

Govindasamy Sekar, Indian Institute of Technology, Madras, India, and colleagues have developed a method to synthesize isoquinolones from N-alkoxy benzamides and alkynes which uses binaphthyl-stabilized palladium nanoparticles (Pd-BNP) as a catalyst. Using a nanocatalyst makes the recovery and reuse of the catalyst easier. The team combined a range of N-alkoxy benzamides with a variety of alkynes in the presence of Pd-BNP, using KI as an additive, air as an oxidant, and dimethylformamide (DMF) as a solvent.

The developed reaction protocol gave a variety of isoquinolones in good to excellent yields. The approach could also be used to synthesize sulfur analogues of isoquinolones from N-methoxybenzothiamide in moderate yields. The Pd-BNP catalyst could easily be recovered by centrifugation and reused up to four times without agglomeration.


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