Nucleophilic substitution of oxazino-/oxazolino-/benzoxazin [3,2-b]indazoles: an effective route to 1H-indazolones.
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.
Donald
Michael B
MB
Department of Chemistry, University of California, One Shields Avenue, Davis, California 95616, USA.
Conrad
Wayne E
WE
Oakdale
James S
JS
Butler
Jeffrey D
JD
Haddadin
Makhluf J
MJ
Kurth
Mark J
MJ
D002384:Catalysis; D003500:Cyclization; D007191:Indazoles / Q000138:chemical synthesis* / Q000737:chemistry*; D008872:Microwaves; D015394:Molecular Structure; D013237:Stereoisomerism
D007191:Indazoles