Preparation of Quinazolinoquinazolinones via a Cascade Approach

Article abstract of DOI:10.1021/acs.joc.8b02239

A one-pot synthesis of quinazolino[3,4-a]quinazolin-13-ones was realized from the direct reaction of o-(methoxycarbonyl)benzenediazonium salts, nitriles, and 2-cyanoanilines in moderate to good yields. This method utilizes the in situ generation of reactive N-arylnitrilium ion, which undergoes further amination/tandem cyclization/amidation to deliver the desired polycyclic scaffolds with consecutive formation of four N-C bonds. Flexibility in substitution patterns, mild reaction conditions, and operational simplicity are the salient features of this methodology.