93970-65-1

Upstream product

• 105363-16-4 (2E)-N-hydroxy-3-phenylacrylimidoyl chloride 
• 104-55-2 3-phenyl-propenal 
• 14371-10-9 (E)-3-phenylpropenal 
• 59336-59-3 cinnamaldehyde oxime 

Downstream Products

• 17819-46-4 5-(4-chloro-phenyl)-3-trans-styryl-4,5-dihydro-isoxazole 
• 17819-40-8 3-trans-styryl-4,5-dihydro-isoxazole-5-carboxylic acid amide 
• 46842-78-8 (3-trans-styryl-[1,2,4]oxadiazol-5-yl)-guanidine 
• 1233234-96-2 (E)-3-styryl-4,5-dihydroisoxazole-5-carboxylic acid 
• 1029697-67-3 (E)-3-styrylisoxazole-5-carboxylic acid 
• 17819-49-7 3-trans-styryl-4,5-dihydro-isoxazole-5-carboxylic acid ethyl ester 
• 130718-55-7 Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-((E)-N-hydroxy-3-phenyl-acrylimidoylsulfanyl)-tetrahydro-pyran-4-yl ester 
• 17819-50-0 4-(5-phenyl-3-trans-styryl-4,5-dihydro-isoxazol-5-yl)-morpholine 

Relevant academic research and scientific papers

Novel access to 2-substituted quinolin-4-ones by nickel boride-mediated reductive ring transformation of 5-(2-nitrophenyl)isoxazoles

Reductive ring transformation of 3-substituted 5-(2-nitrophenyl)isoxazoles, readily accessible via 1,3-dipolar cycloaddition of 2-ethinylnitrobenzene with nitrile oxides, opens a novel access to 2-substituted quinolin-4-ones. Nickel boride, generated in situ from nickel chloride and sodium borohydride, allows, via simultaneous reduction of the nitro group and reductive cleavage of the isoxazole ring, the one-step conversion into the target quinolin-4-ones. This protocol tolerates various functional groups, except olefins, and thus is complementary to the reductive ring transformation with iron/acetic acid, which predominantly tolerates olefins.

Boronic acid catalysis for mild and selective [3+2] dipolar cycloadditions to unsaturated carboxylic acids

Herein, the concept of boronic acid catalysis (BAC) for the activation of unsaturated carboxylic acids is applied in several classic dipolar [3 + 2] cycloadditions involving azides, nitrile oxides, and nitrones as partners. These cycloadditions can be used to produce pharmaceutically interesting, small heterocyclic products, such as triazoles, isoxazoles, and isoxazolidines. These cycloadducts are formed directly and include a free carboxylic acid functionality that can be employed for fur-ther transformations, thereby avoiding prior masking or functionalization. In all cases, BAC provides faster reactions, under milder conditions, with much improved product yields and regioselectivities. In some instances, such as triazole formation from the reaction of azides with 2-alkynoic acids, catalysis with ort/io- nitrophenylboronic acid circumvents the undesirable product decarboxylation observed when using thermal activation. By using NMR spectroscopic studies, the boronic acid catalyst was shown to provide activation by a LUMO-lowering effect in the unsaturated carboxylic acid, likely via a monoacylated hemiboronic ester intermediate.

One-pot copper(I)-catalyzed synthesis of 3,5-disubstituted isoxazoles

3,5-Disubstituted isoxazoles are obtained in good yields by a convenient one-pot, three-step procedure utilizing a regioselective copper(I)-catalyzed cycloaddition reaction between in situ generated nitrile oxides and terminal acetylenes. Most functional

Design and Synthesis of a Piperazinylalkylisoxazole Library for Subtype Selective Dopamine Receptor Ligands

A piperazinylbutylisoxazole library was designed, synthesized and screened for the binding affinities to dopamine D2, D3, and D4 receptors. Several ligands were identified to possess high binding affinity and selectivity for the D3 and D4 receptors over the D2 receptor. Compounds 6s and 6t showed Ki values of 2.6 nM and 3.9 nM for the D3 receptor with 46- and 50-fold selectivity over te D2 receptor, respectively.