title: Nucleophilic substitution of oxazino-/oxazolino-/benzoxazin [3,2-b]indazoles: an effective route to 1H-indazolones.
abstract: A variety of nucleophiles, thiolates, alkoxides, amines, iodide, and cyanide, react with oxazino-, oxazolino-, and benzoxazin[3,2-b]indazoles under microwave conditions to yield a diverse set of 2-substituted 1H-indazolones. The synthetic utility of these indazoles is further demonstrated by ANRORC (addition of the nucleophile, ring-opening, and ring closure) reactions to yield isomeric pyrazoloindazolones by a process wherein iodide acts first as a nucleophile and subsequently as a leaving group.
authors.affiliation: Department of Chemistry, University of California, One Shields Avenue, Davis, California 95616, USA.
authors.forename: Michael B
authors.initials: MB
authors.lastname: Donald
authors.forename: Wayne E
authors.initials: WE
authors.lastname: Conrad
authors.forename: James S
authors.initials: JS
authors.lastname: Oakdale
authors.forename: Jeffrey D
authors.initials: JD
authors.lastname: Butler
authors.forename: Makhluf J
authors.initials: MJ
authors.lastname: Haddadin
authors.forename: Mark J
authors.initials: MJ
authors.lastname: Kurth
mesh_terms: D002384:Catalysis; D003500:Cyclization; D007191:Indazoles / Q000138:chemical synthesis* / Q000737:chemistry*; D008872:Microwaves; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D007191:Indazoles