Acid and base catalyzed Davis-Beirut reaction: experimental and theoretical mechanistic studies and synthesis of novel 3-amino-2H-indazoles

TETRAHEDRON LETTERS

卷:53

Article

Avila, Belem¹  El-Dakdouki, Mohammad H.²  Nazer, Musa Z.³  Harrison, Jason G.¹  Tantillo, Dean J.¹  Haddadin, Makhluf J.²  Kurth, Mark J.¹ 

[1] Univ Calif Davis, Dept Chem, Davis, CA 95616 USA

[2] Amer Univ Beirut, Dept Chem, Beirut, Lebanon

[3] Univ Jordan, Dept Chem, Amman, Jordan

关键词: Davis-Beirut reaction;    2H-Indazole;    o-Nitrosobenzaldehyde;    Mechanism;    Catalysis;   

DOI  :  10.1016/j.tetlet.2012.09.026

来源: Elsevier

【 摘 要 】

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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