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 Citations (Scopus)

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

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Indazoles
Theoretical Models
Acids
Imines
Catalysis
Amines
Derivatives

Keywords

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

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

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

Acid and base catalyzed Davis-Beirut reaction : Experimental and theoretical mechanistic studies and synthesis of novel 3-amino-2H-indazoles. / Avila, Belem; El-Dakdouki, Mohammad H.; Nazer, Musa Z.; Harrison, Jason G.; Tantillo, Dean J.; Haddadin, Makhluf J.; Kurth, Mark J.

In: Tetrahedron Letters, Vol. 53, No. 48, 28.11.2012, p. 6475-6478.

Research output: Contribution to journalArticle

Avila, B, El-Dakdouki, MH, Nazer, MZ, Harrison, JG, Tantillo, DJ, Haddadin, MJ & Kurth, MJ 2012, 'Acid and base catalyzed Davis-Beirut reaction: Experimental and theoretical mechanistic studies and synthesis of novel 3-amino-2H-indazoles', Tetrahedron Letters, vol. 53, no. 48, pp. 6475-6478. https://doi.org/10.1016/j.tetlet.2012.09.026
Avila, Belem ; El-Dakdouki, Mohammad H. ; Nazer, Musa Z. ; Harrison, Jason G. ; Tantillo, Dean J. ; Haddadin, Makhluf J. ; Kurth, Mark J. / Acid and base catalyzed Davis-Beirut reaction : Experimental and theoretical mechanistic studies and synthesis of novel 3-amino-2H-indazoles. In: Tetrahedron Letters. 2012 ; Vol. 53, No. 48. pp. 6475-6478.
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