A two-step synthesis of 5-aminoisoxazoles from olefins

✍ Scribed by Martin Dines; M.L. Scheinbaum

• Book ID: 104240144
• Publisher: Elsevier Science
• Year: 1969
• Tongue: French
• Weight: 113 KB
• Volume: 10
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)88818-3

✦ Synopsis

Synthetic approaches to 5-aminoisoxazoles have involved, for the most part, reactions of hydroxylamine with either m-substituted nitriles (2) or amidines (3) or with cyanoacetylenes (4). We wish to report a facile, high yield pathway to 3,4-disubstituted-S-aminoisoxasoles (I) comprising two synthetic steps from olefins. The method involves treatment of olefinnitrosyl chloride adducts with inorganic cyanide in acetonitrile to give I directly.