Acid and base catalyzed Davis–Beirut reaction: experimental and theoretical mechanistic studies and synthesis of novel 3-amino-2H-indazoles
作者:Belem Avila、Mohammad H. El-Dakdouki、Musa Z. Nazer、Jason G. Harrison、Dean J. Tantillo、Makhluf J. Haddadin、Mark J. Kurth
DOI:10.1016/j.tetlet.2012.09.026
日期:2012.11
2H-indazoles and, subsequently, indazolones, is shown to proceed rapidly from o-nitrosobenzaldehyde and primaryamines 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