Insertion of benzene rings into the amide bond: one-step synthesis of acridines and acridones from aryl amides

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Abstract

"Chemical Equation Presented" 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. © 2010 American Chemical Society.

Bibliographical metadata

Original languageEnglish
Pages (from-to)168-171
Number of pages3
JournalOrganic Letters
Volume12
Issue number1
DOIs
StatePublished - 1 Jan 2010