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 Citations (Scopus)

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

Fingerprint

Indazoles
Nucleophiles
nucleophiles
Iodides
Substitution reactions
routes
substitutes
iodides
Cyanides
Microwaves
Amines
rings
alkoxides
cyanides
closures
amines
microwaves

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry

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

Nucleophilic substitution of oxazino-/oxazolino-/benzoxazin [3,2- b ]indazoles : An effective route to 1 H-indazolones. / Donald, Michael B.; Conrad, Wayne E.; Oakdale, James S.; Butler, Jeffrey D.; Haddadin, Makhluf J.; Kurth, Mark J.

In: Organic Letters, Vol. 12, No. 11, 04.06.2010, p. 2524-2527.

Research output: Contribution to journalArticle

Donald, MB, Conrad, WE, Oakdale, JS, Butler, JD, Haddadin, MJ & Kurth, MJ 2010, 'Nucleophilic substitution of oxazino-/oxazolino-/benzoxazin [3,2- b ]indazoles: An effective route to 1 H-indazolones', Organic Letters, vol. 12, no. 11, pp. 2524-2527. https://doi.org/10.1021/ol100751n
Donald, Michael B. ; Conrad, Wayne E. ; Oakdale, James S. ; Butler, Jeffrey D. ; Haddadin, Makhluf J. ; Kurth, Mark J. / Nucleophilic substitution of oxazino-/oxazolino-/benzoxazin [3,2- b ]indazoles : An effective route to 1 H-indazolones. In: Organic Letters. 2010 ; Vol. 12, No. 11. pp. 2524-2527.
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