Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
5265444 | Tetrahedron Letters | 2012 | 4 Pages |
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.
Keywords
Related Topics
Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Belem Avila, Mohammad H. El-Dakdouki, Musa Z. Nazer, Jason G. Harrison, Dean J. Tantillo, Makhluf J. Haddadin, Mark J. Kurth,