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

22 Scopus citations

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

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry

Fingerprint Dive into the research topics of 'A one-pot-three-step route to triazolotriazepinoindazolones from oxazolino-2H-indazoles'. Together they form a unique fingerprint.

  • 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