A Ligand-Free Pd-Catalyzed Cascade Reaction: An Access to the Highly Diverse Isoquinolin-1(2H)-one Derivatives via Isocyanide and Ugi-MCR Synthesized Amide Precursors

• Published in: Organic letters Vol. 14; no. 12; pp. 3126 - 3129
• Main Authors: Tyagi, Vikas, Khan, Shahnawaz, Giri, Archana, Gauniyal, Harsh M, Sridhar, B, Chauhan, Prem M. S
• Format: Journal Article
• Language: English
• Published: United States American Chemical Society 15-06-2012
• Subjects: Amides - chemical synthesis; Amides - chemistry; Catalysis; Cyanides - chemistry; Cyclization; Isoquinolines - chemistry; Ligands; Models, Molecular; Molecular Structure; Palladium - chemistry
• ISSN: 1523-7060; 1523-7052
• DOI: 10.1021/ol301131s

A novel ligand-free palladium-catalyzed cascade reaction for the synthesis of highly diverse isoquinolin-1(2H)-one derivatives from isocyanide and amide precursors synthesized by Ugi-MCR has been developed. A broad variety of acids, amines, and isocyanides were used as starting materials for Ugi-MCR leading to various amide precursors, which in turn provided entry into diverse isoquinolin-1(2H)-one derivatives. The reaction proceeds through tandem isocyanide insertion with intramolecular cyclization followed by a Mazurciewitcz–Ganesan type sequence to provide isoquinoline-1(2H)-one derivatives in moderate to good yields.