期刊
TETRAHEDRON LETTERS
卷 53, 期 48, 页码 6475-6478出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2012.09.026
关键词
Davis-Beirut reaction; 2H-Indazole; o-Nitrosobenzaldehyde; Mechanism; Catalysis
资金
- National Science Foundation [CHE-0910870]
- National Institutes of Health [GM089153]
- United States Department of Education
- Bristol-Myers Squibb
- Alfred P. Sloan Minority Ph.D. Program
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. (C) 2012 Elsevier Ltd. All rights reserved.
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