title: Synthesis of o-(dimethylamino)aryl ketones, acridones, acridinium salts, and 1H-indazoles by the reaction of hydrazones and arynes.
abstract: A novel, efficient route to biologically and pharmaceutically important o-(dimethylamino)aryl ketones, acridones, acridinium salts, and 1H-indazoles has been developed starting from readily available hydrazones of aldehydes and o-(trimethylsilyl)aryl triflates. The reaction proceeds through arynes under mild conditions, tolerates a wide range of functional groups, and provides the final products in good to excellent yields.
authors.affiliation: Department of Chemistry, Iowa State University, Ames, Iowa 50011, USA.
authors.forename: Anton V
authors.initials: AV
authors.lastname: Dubrovskiy
authors.forename: Richard C
authors.initials: RC
authors.lastname: Larock
mesh_terms: D000166:Acridines / Q000138:chemical synthesis* / Q000737:chemistry; D054831:Acridones; D001555:Benzene Derivatives / Q000737:chemistry*; D060326:Chemistry Techniques, Synthetic; D003500:Cyclization; D054879:Halogenation; D006835:Hydrazones / Q000737:chemistry*; D007097:Imines / Q000737:chemistry; D007191:Indazoles / Q000138:chemical synthesis* / Q000737:chemistry; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D009570:Nitriles / Q000737:chemistry; D012492:Salts / Q000737:chemistry*
chemical_list: D000166:Acridines; D054831:Acridones; D001555:Benzene Derivatives; D006835:Hydrazones; D007097:Imines; D007191:Indazoles; D007659:Ketones; D009570:Nitriles; D012492:Salts; C524146:benzyne; C542835:ketimine; C041300:acridone