Acid and base catalyzed Davis-Beirut reaction: Experimental and theoretical mechanistic studies and synthesis of novel 3-amino-2H-indazoles

Belem Avila, Mohammad H. El-Dakdouki, Musa Z. Nazer, Jason G. Harrison, Dean J. Tantillo, Makhluf J. Haddadin, Mark J. Kurth

Research output: Contribution to journalArticle

16 Scopus citations

Abstract

The Davis-Beirut reaction, which provides an efficient synthesis of 2H-indazoles and, subsequently, indazolones, is shown to proceed rapidly from o-nitrosobenzaldehyde and primary amines under both acid and base catalysis. Experimental and theoretical evidence in support of a reaction mechanism is provided in which o-nitrosobenzylidine imine is a pivotal intermediate in this N,N-bond forming heterocyclization reaction. The Davis-Beirut reaction is also shown to effectively synthesize a number of novel 3-amino-2H-indazole derivatives.

Original languageEnglish (US)
Pages (from-to)6475-6478
Number of pages4
JournalTetrahedron Letters
Volume53
Issue number48
DOIs
StatePublished - Nov 28 2012

Keywords

  • 2H-Indazole
  • Catalysis
  • Davis-Beirut reaction
  • Mechanism
  • o-Nitrosobenzaldehyde

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

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    Avila, B., El-Dakdouki, M. H., Nazer, M. Z., Harrison, J. G., Tantillo, D. J., Haddadin, M. J., & Kurth, M. J. (2012). Acid and base catalyzed Davis-Beirut reaction: Experimental and theoretical mechanistic studies and synthesis of novel 3-amino-2H-indazoles. Tetrahedron Letters, 53(48), 6475-6478. https://doi.org/10.1016/j.tetlet.2012.09.026