83670-85-3

Upstream product

• 1198015-31-4 3-methylene-5-phenyl-2-(trimethylsilyloxy)isoxazolidine 
• 407-25-0 trifluoroacetic anhydride 
• 100-42-5 styrene 
• 83967-98-0 5-Phenyl-3-(tetrahydro-pyran-2-yloxymethyl)-4,5-dihydro-isoxazole 
• 7064-04-2 ethyl 5-phenyl-2-isoxazoline-3-carboxylate 

Downstream Products

• 80061-95-6 3-chloromethyl-5-phenylisoxazoline 
• 3480-87-3 3-hydroxy-3-phenylpropanoic acid 
• 7497-61-2 methyl 3-hydroxy-3-phenylpropionate 
• 154153-26-1 C-(5-phenyl-4,5-dihydro-isoxazol-3-yl)-methylamine 
• 109000-39-7 (S)-5-Phenyl-4,5-dihydro-isoxazole-3-carbaldehyde 
• 83670-90-0 1,4-Dihydroxy-4-phenyl-butan-2-one 

Relevant academic research and scientific papers

Reaction of n,n-dioxyenamines with anhydrides of carboxylic and sulfonic acids; A new method for the synthesis of a-hydroxyoxime derivatives

The reactions of N,N-dioxyenamines with carboxylic and sulfonic acid anhydrides were investigated. A new method for the synthesis of a-hydroxyoxime derivatives via the reaction of N,N-dioxyenamines with trifluoroacetic anhydride is described.

SUBSTITUTED HETEROCYCLIC COMPOUNDS USEFUL IN THE TREATMENT OF CARDIOVASCULAR DISEASES

wherein: a.o. T is oxygen, sulfur, or NR11 , in which R11 is hydrogen or lower alkyl; V is -N1 is hydrogen, optionally substituted lower alkyl, optionally substituted cycloalkyl, optionally substituted aryl, or optionally substituted heteroaryl; X2 is optionally substituted aryl or optionally substituted heteroaryl; Y is optionally substituted dihydroheteroarcyl; and Z1 and Z2 are independently optionally substituted alkylene of 1-4 carbon atoms, useful for the treatment of various disease states, in particular cardiovascular diseases such as atrial and ventricular arrhythmias, intermittent claudication, Prinzmetal’s (variant) angina, stable and unstable angina, exercise induced angina, congestive heart disease, and myocardial infarction. The compounds are also useful in the treatment of diabetes.

Anti-influenza virus activities of 2-alkoxyimino-N-(2-isoxazolin-3-ylmethyl)acetamides

A series of 2-alkoxyimino-N-(2-isoxazolin-3-ylmethyl)acetamides and related compounds were synthesized and their antiviral activities against human influenza A virus were assessed. Studies of the structure-activity relationships revealed the strongest antiviral activity when position-5 of the isoxazoline ring was substituted with a tert-butyl group. When the alkoxyimino moiety was substituted with a methyl, ethyl, isopropyl or allyl group, good antiviral activity was obtained. Among the geometrical isomers at the oxime moiety, the E-isomers were more active than the Z-isomers. Among the compounds examined, (E)-2-allyloxyimino-2-cyano-N-(5-tert-butyl-2-isoxazolin-3-ylmethyl)acetamide (1j) was the most active inhibitor with an EC50 of 3 μg/mL in vitro.

METAL-HYDRIDE REDUCTION OF ISOXAZOLINE-3-CARBOXYLATE ESTERS

The reduction of a series of isoxazoline-3-carboxylate esters with sodium borohydride gave 3-(hydroxymethyl)isoxazolines in 34-98percent yield.Reduction with DIBAH gave isoxazoline-3-carboxaldehydes in 63 and 85percent yields for the two reactions studied

Methods for the Stereoselective Cis Cyanohydroxylation and Carboxyhydroxylation of Olefins

Two valuable reagents for the cis-specific vicinal cyanohydroxylation and carboxyhydroxylation of olefins are described.The cyanohydroxylation process is based on the decarboxylative ring opening of 3-carboxyisoxazolines prepared by the cycloaddition reaction of carbethoxyformonitrile oxide with various alkenes.Fragmentation of the isoxazolines prepared from cis- and trans-2-butene has been found to occur without any crossover in stereochemistry.The carboxyhydroxylation process begins with the dipolar cycloaddition reaction of the nitrile oxide derived from thetetrahydropyranyl ether derivative of 2-nitroethanol.Deprotection, hydrogenation, and oxitative cleavage of the derived dihydroxy ketone yield the stereochemcally pure β-hydroxy carboxylic acid.