A convenient synthesis of 4-alkyl-5-aminoisoxazoles.
[reaction: see text] A series of 4-alkyl-5-aminoisoxazoles have been synthesized in high yield by nucleophilic addition of lithiated alkyl nitriles to (alpha)-chlorooximes. The scope and limitations of this reaction were examined by varying the nature of the nitrile and chloride oxime.
Bourbeau
Matthew P
MP
Department of Medicinal Chemistry, Amgen Inc., 1 Amgen Center Drive, Thousand Oaks, California 91303, USA. bourbeau@amgen.com
Rider
James T
JT
D000478:Alkylation; D000588:Amines / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D007555:Isoxazoles / Q000138:chemical synthesis* / Q000737:chemistry; D009570:Nitriles / Q000737:chemistry*; D010091:Oximes
D000588:Amines; D007555:Isoxazoles; D009570:Nitriles; D010091:Oximes