51978-98-4

Upstream product

• 1123-49-5 3,5-dimethyl-4-nitroisoxazole 
• 123-11-5 4-methoxy-benzaldehyde 

Downstream Products

• 103806-30-0 2-Acetyl-3-(4-methoxy-phenyl)-4-(3-methyl-4-nitro-isoxazol-5-yl)-butyric acid ethyl ester 
• 79510-68-2 5-(4-Methoxy-phenyl)-3'-methyl-4'-nitro-3-phenyl-4,5-dihydro-[4,5']biisoxazolyl 
• 943-89-5 (E)-3-(4-methoxyphenyl)acrylic acid 
• 754985-40-5 4-amino-3-methyl-5-[(E)-2-(4-methoxyphenyl)-1-ethenyl]isoxazole 
• 98239-37-3 5-[2-(3,5-Dimethyl-1H-pyrazol-4-yl)-2-(4-methoxy-phenyl)-ethyl]-3-methyl-4-nitro-isoxazole 
• 98239-48-6 5-[2-(3,5-Dimethyl-1-phenyl-1H-pyrazol-4-yl)-2-(4-methoxy-phenyl)-ethyl]-3-methyl-4-nitro-isoxazole 
• 1205553-70-3 (S)-5-(2-(4-methoxyphenyl)-3-nitropropyl)-3-methyl-4-nitroisoxazole 
• 1205553-75-8 (R)-5-(2-(4-methoxyphenyl)-3-nitropropyl)-3-methyl-4-nitroisoxazole 

Relevant academic research and scientific papers

Catalytic enantioselective addition of isocyanoacetate to 3-methyl-4-nitro-5-styrylisoxazoles under phase transfer catalysis conditions

The reaction between 3-methyl-4-nitro-5-styrylisoxazoles and ethyl isocyanoacetate proceeded under phase transfer catalysis to give enantioenriched monoadducts in high enantiomeric excess (up to 99% ee). The resulting adducts were subsequently cyclised to give 2,3-dihydropyrroles and substituted pyrrolidines in identical high ees and as a single diastereoisomer.

Trifluoromethylation of aromatic isoxazoles: Regio- and diastereoselective route to 5-trifluoromethyl-2-isoxazolines

It all adds up: The activation of aromatic isoxazoles with a nitro group at the 4-position has enabled the first regio- and diastereoselective trifluoromethylation at the 5-position of isoxazoles by nucleophilic addition using Me3SiCF3 (see scheme; DMF=N,N′- dimethylformamide). The process was demonstrated with a broad range of 3,5-aromatic, heteroaromatic and aliphatic substrates.

Catalytic asymmetric conjugate addition of nitroalkanes to 4-nitro5-styrylisoxazoles

(Chemical equation presented) Nitro versus nitro: 4-Nitro-5- styrylisoxazoles were used as masked α,β-unsaturated carboxylic acids in the titled catalytic asymmetric transformation. The 4-nitroisoxazole core acts as an activator of the conjugated alkene and a latent carboxylate functionality. The reaction proceeded with 5 mol% of a readily prepared phasetransfer catalyst at room temperature with remarkable diastereo- and enantioselectivity (see scheme).

Chemistry of Heterocylces: Part VIII - Synthesis of Isoxazolylethylpyrazoles

The base-catalysed addition of acetylacetone to 3-methyl-4-nitro-5-styrylisoxazoles (II) leads to the Michael adducts 3-pentane-2,4-diones (III).These β-diketones (III) undergo cyclization with hydrazine sulphate and phenylhydrazine to furnish pyrazoles (IV) and N-phenylpyrazoles (V), respectively.