Reaction of β-dimethylaminovinyl ketones with hydroxylamine: A simple and useful method for synthesis of 3- and 5-substituted isoxazoles

✍ Scribed by Fernanda A. Rosa; Pablo Machado; Helio G. Bonacorso; Nilo Zanatta; Marcos A. P. Martins

• Publisher: Journal of Heterocyclic Chemistry
• Year: 2008
• Tongue: English
• Weight: 486 KB
• Volume: 45
• Category: Article
• ISSN: 0022-152X
• DOI: 10.1002/jhet.5570450337

✦ Synopsis

The regioselective synthesis of 3-and 5-substituted-isoxazoles from the reaction of β-dimethylaminovinyl ketones [R-C(O)CH=CH-NMe 2 , where R = Ph, MeO-4-C 6 H 4 , F-4-C 6 H 4 , Cl-4-C 6 H 4 , Br-4-C 6 H 4 , O 2 N-4-C 6 H 4 , fur-2-yl, thien-2-yl, pyrrol-2-yl, Et and CCl 3 ] and hydroxylamine hydrochloride varying only the reaction conditions (with and without the addition of pyridine) is reported.