A one-pot-three-step route to triazolotriazepinoindazolones from oxazolino-2H-indazoles

Wayne E. Conrad, Kevin X. Rodriguez, Huy H. Nguyen, James C. Fettinger, Makhluf J. Haddadin, Mark J. Kurth

Research output: Contribution to journalArticle

21 Citations (Scopus)

Abstract

A one-pot-three-step method has been developed for the conversion of oxazolino-2H-indazoles into triazolotriazepinoindazolones with three points of diversity. Step one of this process involves a propargyl bromide-initiated ring opening of the oxazolino-2H-indazole (available by the Davis-Beirut reaction) to give an N1-(propargyl)-N2-(2-bromoethyl)-disubstituted indazolone, which then undergoes -CH2Br → -CH2N 3 displacement (step two) followed by an uncatalyzed intramolecular azide-alkyne 1,3-dipolar cycloaddition (step three) to form the target heterocycle. Employing 7-bromooxazolino-2H-indazole allows for further diversification through, for example, palladium-catalyzed coupling chemistry, as reported here.

Original languageEnglish (US)
Pages (from-to)3870-3873
Number of pages4
JournalOrganic Letters
Volume14
Issue number15
DOIs
StatePublished - Aug 3 2012

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Indazoles
routes
Alkynes
Azides
Cycloaddition
Cycloaddition Reaction
Palladium
cycloaddition
alkynes
palladium
bromides
chemistry
rings

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry

Cite this

Conrad, W. E., Rodriguez, K. X., Nguyen, H. H., Fettinger, J. C., Haddadin, M. J., & Kurth, M. J. (2012). A one-pot-three-step route to triazolotriazepinoindazolones from oxazolino-2H-indazoles. Organic Letters, 14(15), 3870-3873. https://doi.org/10.1021/ol3015804

A one-pot-three-step route to triazolotriazepinoindazolones from oxazolino-2H-indazoles. / Conrad, Wayne E.; Rodriguez, Kevin X.; Nguyen, Huy H.; Fettinger, James C.; Haddadin, Makhluf J.; Kurth, Mark J.

In: Organic Letters, Vol. 14, No. 15, 03.08.2012, p. 3870-3873.

Research output: Contribution to journalArticle

Conrad, WE, Rodriguez, KX, Nguyen, HH, Fettinger, JC, Haddadin, MJ & Kurth, MJ 2012, 'A one-pot-three-step route to triazolotriazepinoindazolones from oxazolino-2H-indazoles', Organic Letters, vol. 14, no. 15, pp. 3870-3873. https://doi.org/10.1021/ol3015804
Conrad WE, Rodriguez KX, Nguyen HH, Fettinger JC, Haddadin MJ, Kurth MJ. A one-pot-three-step route to triazolotriazepinoindazolones from oxazolino-2H-indazoles. Organic Letters. 2012 Aug 3;14(15):3870-3873. https://doi.org/10.1021/ol3015804
Conrad, Wayne E. ; Rodriguez, Kevin X. ; Nguyen, Huy H. ; Fettinger, James C. ; Haddadin, Makhluf J. ; Kurth, Mark J. / A one-pot-three-step route to triazolotriazepinoindazolones from oxazolino-2H-indazoles. In: Organic Letters. 2012 ; Vol. 14, No. 15. pp. 3870-3873.
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