ChemInform Abstract: Palladium‐Catalyzed Double Carbonylation‐Based Diversity‐Oriented Synthesis of 3,4‐Dihydroisoquinoline‐1‐carboxamides.

Abstract

Palladium-Catalyzed Double Carbonylation-Based Diversity-Oriented Synthesis of 3,4-Dihydroisoquinoline-1-carboxamides. -A novel synthetic methodology for the generation of dihydroisoquinoline carboxamides and its analogues is developed. First, the initial palladium-catalyzed double carbonylation of an N-protected aryl iodide and an amine partner affords intermediate -keto carboxamides. Subsequent treatment with trifluoroacetic acid leads to deprotection and intramolecular imine formation to afford the isoquinoline products. Isoindole (VIII) and benzoazepine (XI) carboxamide derivatives are obtained under similar conditions. -(MASUI, H.; ISHIZAWA, N.; FUSE, S.; TAKAHASHI*, T.; Tetrahedron 71 (2015) 37, 6354-6360, http://dx.