Nucleophilic substitution of oxazino-/oxazolino-/benzoxazin [3,2- b ]indazoles: An effective route to 1 H-indazolones

Michael B. Donald, Wayne E. Conrad, James S. Oakdale, Jeffrey D. Butler, Makhluf J. Haddadin, Mark J. Kurth

Research output: Contribution to journalArticle

21 Scopus citations

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.

Original languageEnglish (US)
Pages (from-to)2524-2527
Number of pages4
JournalOrganic Letters
Volume12
Issue number11
DOIs
StatePublished - Jun 4 2010

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry

Fingerprint Dive into the research topics of 'Nucleophilic substitution of oxazino-/oxazolino-/benzoxazin [3,2- b ]indazoles: An effective route to 1 H-indazolones'. Together they form a unique fingerprint.

  • Cite this

    Donald, M. B., Conrad, W. E., Oakdale, J. S., Butler, J. D., Haddadin, M. J., & Kurth, M. J. (2010). Nucleophilic substitution of oxazino-/oxazolino-/benzoxazin [3,2- b ]indazoles: An effective route to 1 H-indazolones. Organic Letters, 12(11), 2524-2527. https://doi.org/10.1021/ol100751n