Davis–Beirut reaction

In chemistry the Davis–Beirut reaction is an annulation reaction first reported by Mark Kurth and Makhluf Haddadin in 2005.[1] It is named after their respective universities; University of California, Davis and American University of Beirut.[2][3]

The reaction originally produced N2-substituted-indazalones, by a reaction between o-nitrosobenzaldehyde and primary amines, under basic conditions.[1] It has subsequently been expanded to produce a variety of 3-hetero-indazoles from a boarder range of starting materials[4][5] under acidic or basic conditions.[6]

References

  1. 1 2 Kurth, Mark J.; Olmstead, Marilyn M.; Haddadin, Makhluf J. (2005). "Claimed 2,1-Benzisoxazoles Are Indazalones". The Journal of Organic Chemistry. 70 (3): 1060–1062. doi:10.1021/jo048153i. ISSN 0022-3263.
  2. ↑ Conrad, Wayne E.; Fukazawa, Ryo; Haddadin, Makhluf J.; Kurth, Mark J. (2011). "The Davis–Beirut Reaction:N1,N2-Disubstituted-1H-Indazolones via 1,6-Electrophilic Addition to 3-Alkoxy-2H-Indazoles". Organic Letters. 13 (12): 3138–41. doi:10.1021/ol2010424. PMC 3112251Freely accessible. PMID 21612219.
  3. ↑ "'Davis-Beirut Reaction': Town recognizes gown, and vice versa". 30 Aug 2013.
  4. ↑ Mills, Aaron D.; Nazer, Musa Z.; Haddadin, Makhluf J.; Kurth, Mark J. (2006). "N,N-Bond-Forming Heterocyclization: Synthesis of 3-Alkoxy-2H-indazoles". The Journal of Organic Chemistry. 71 (7): 2687–2689. doi:10.1021/jo0524831. ISSN 0022-3263.
  5. ↑ Schmidt, Andreas; Beutler, Ariane; Snovydovych, Bohdan (2008). "Recent Advances in the Chemistry of Indazoles". European Journal of Organic Chemistry. 2008 (24): 4073–4095. doi:10.1002/ejoc.200800227. ISSN 1434-193X.
  6. ↑ Avila, Belem; El-Dakdouki, Mohammad H.; Nazer, Musa Z.; Harrison, Jason G.; Tantillo, Dean J.; Haddadin, Makhluf J.; Kurth, Mark 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. doi:10.1016/j.tetlet.2012.09.026. ISSN 0040-4039.


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