99298-80-3

Upstream product

• 18718-83-7 4-chloromethyl-5-methyl-3-phenyl-isoxazole 
• 93599-35-0 4-(4',5'-dihydro-4',4'-dimethyl-Δ²-oxazolin-2-yl)-3,5-dimethylisoxazole 
• 17147-85-2 3-ethyl-5-methyl-isoxazole-4-carboxylic acid 
• 99298-90-5 3-ethyl-5-methyl-4-isoxazole carbonyl chloride 
• 99298-91-6 3-Ethyl-5-methyl-isoxazole-4-carboxylic acid (2-hydroxy-1,1-dimethyl-ethyl)-amide 
• 2510-36-3 3,5-dimethyl-4-isoxazolecarboxylic acid 

Relevant academic research and scientific papers

Metalation of Isoxazolyloxazolines, a Facile Route to Functionally Complex Isoxazoles: Utility, Scope, and Comparison to Dianion Methodology

2-(5'-Alkylisoxazol-4'-yl)-Δ2-oxazoline was metalated at the C-5' alkyl group, and the lithio anion was quenched with a variety of electrophiles.Alkyl halides, aldehydes, and acylpyridinium salts were used as electrophiles.The lithio anion was oxygenated with MOOPH or N-(phenylsulfonyl)oxaziridene.The isoxazolyloxazoline system was converted to the isoxazolyl carboxylic acid, aldehyde, ketone, and chiral oxazoline.The isoxazolyloxazoline was formed, metalated, and deprotected in synthetically useful yields and represents a facile entry into functionally complex isoxazoles.To determine the necessity of the oxazoline protection/deprotection scheme, dianions of isoxazole-4-carboxylic acids were studied.The dianion method was found to be more efficient for simple alkyl halides, but limited in scope.

A FACILE SYNTHESIS OF FUNCTIONALLY COMPLEX ISOXAZOLE DERIVATIVES

Metalation of 2(4'-Isoxazolyl)-Δ2-oxazolines takes place initially and selectively on the C-5'-alkyl group.Subsequent metalation also proceeds at this position.Selective deprotection of the oxazoline was accomplished without disturbing the izox