title: Acid and base catalyzed Davis-Beirut reaction: experimental and theoretical mechanistic studies and synthesis of novel 3-amino-2H-indazoles.
abstract: The Davis-Beirut reaction, which provides an efficient synthesis of 2H-indazoles and, subsequently, indazolones, is shown to proceed rapidly from o-nitrosobenzaldehyde and primary amines under both acid or base catalysis. Experimental and theoretical evidence in support of a reaction mechanism is provided in which o-nitrosobenzylidine imine is a pivotal intermediate in this N,N-bond forming heterocyclization reaction. The Davis-Beirut reaction is also shown to effectively synthesize a number of novel 3-amino-2H-indazole derivatives.
authors.affiliation: Department of Chemistry, University of California, One Shields Avenue, Davis, California 95616.
authors.forename: Belem
authors.initials: B
authors.lastname: Avila
authors.forename: Mohammad H
authors.initials: MH
authors.lastname: El-Dakdouki
authors.forename: Musa Z
authors.initials: MZ
authors.lastname: Nazer
authors.forename: Jason G
authors.initials: JG
authors.lastname: Harrison
authors.forename: Dean J
authors.initials: DJ
authors.lastname: Tantillo
authors.forename: Makhluf J
authors.initials: MJ
authors.lastname: Haddadin
authors.forename: Mark J
authors.initials: MJ
authors.lastname: Kurth