Nucleophilic Substitution of Oxazino-/Oxazolino-/Benzoxazin [3,2- b ]indazoles: An Effective Route to 1 H -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 1 H -indazolones. The synthetic utility of these indazoles is further demonstrated by A...

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Bibliographic Details
Published in:Organic letters 2010-06, Vol.12 (11), p.2524-2527
Main Authors: Donald, Michael B., Conrad, Wayne E., Oakdale, James S., Butler, Jeffrey D., Haddadin, Makhluf J., Kurth, Mark J.
Format: Article
Language:English
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Summary: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 1 H -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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol100751n