Insertion of benzene rings into the amide bond: one-step synthesis of acridines and acridones from aryl amides.
Insertion of benzene rings into the amide bond using the reactive intermediate benzyne is described. Aromatic amides undergo smooth insertion when treated with O-triflatophenyl silane benzyne precursors, producing versatile aminobenzophenone products in good to excellent yield. The process is entirely metal-free and has been exemplified on the synthesis of biologically active acridones and acridines.
Pintori
Didier G
DG
School of Chemistry, University of Edinburgh, King's Buildings, West Mains Rd, Edinburgh EH9 3JJ, UK.
Greaney
Michael F
MF