35100-96-0

Upstream product

• 175789-99-8 2,4-dinitro-3-phenyl-pentanedioic acid dimethyl ester 
• 53431-72-4 α-nitro cinnamate de methyle 
• 75-31-0 isopropylamine 
• 2483-57-0 methyl 2-nitroacetate 
• 27845-51-8 (E)-N-benzylidenepropan-2-amine 
• 100-52-7 benzaldehyde 

Downstream Products

• 34587-96-7 4-phenyl-isoxazole-3,5-dicarboxylic acid bis-butylamide 
• 74640-77-0 methyl α-hydroxy-2-methoxycarbonyl-1-oxido-3H-indole-3-acetate 
• 74640-78-1 trans-3,5-bis(methoxycarbonyl)-4-phenyl-2-isoxazoline 
• 74647-73-7 5-Butylcarbamoyl-3-methoxycarbonyl-4-phenylisoxazoline N-Oxide 
• 74647-68-0 (4S,5S)-2-Oxy-4-phenyl-4,5-dihydro-isoxazole-3,5-dicarboxylic acid bis-butylamide 
• 74647-76-0 (4S,5S)-5-(4-Nitro-benzoyloxymethyl)-2-oxy-4-phenyl-4,5-dihydro-isoxazole-3-carboxylic acid methyl ester 
• 74647-74-8 percent-Ethoxycarbonyl-3-methoxycarbonyl-4-phenylisoxazoline N-Oxide 
• 97053-55-9 methyl 2-methoxycarbonyl-α-(p-nitrobenzoyloxy)-1-oxido-3H-indole-3-acetate 
• 97053-54-8 methyl α-benzyloxy-2-methoxycarbonyl-1-oxido-3H-indole-3-acetate 

Relevant academic research and scientific papers

Comparison of Substituting Ability of Nitronate versus Enolate for Direct Substitution of a Nitro Group

α-Nitrocinnamate underwent the conjugate addition of an active methylene compound such as nitroacetate, 1,3-dicarbonyl compound, or α-nitroketone, and the following ring closure afforded functionalized heterocyclic frameworks. The reaction of cinnamate with nitroacetate occurs via nucleophilic substitution of a nitro group by the O-attack of the nitronate, which results in isoxazoline N-oxide. This protocol was applicable to 1,3-dicarbonyl compounds to afford dihydrofuran derivatives, including those derived from direct substitution of a nitro group caused by O-attack of enolate. It was found the reactivity was lowered by an electron-withdrawing group on the carbonyl moiety. When α-nitroketone was employed as a substrate, three kinds of products were possibly formed; of these, only isoxazoline N-oxide was identified. This result indicates that the substituting ability of nitronate is higher than that of enolate for the direct SN2 substitution of a nitro group.

Highly diastereoselective condensation of α-nitro-esters with aldehydes catalyzed by zinc complexes of amino acids

Zinc complexes of amino acids efficiently catalyze the condensation between α-nitro-esters and a variety of aldehydes. An unusual domino reaction sequence leads to the diastereoselective formation of substituted isoxazoline N-oxides in high yields.

A Convenient One-Pot Synthesis of 4-Substituted 3,5-Bis(alkoxycarbonyl)-4,5-dihydroisoxazole 2-Oxides from Aldehydes and Nitroacetic Esters in a Solid-Liquid Reaction System and Subsequent Deoxygenation

4-Substituted 3,5-bis(alkoxycarbonyl)-4,5-dihydroisoxazole 2-oxides are obtained from nitroacetic esters and imines which are prepared from aldehydes and isopropylamine in the presence of molecular sieves.Reduction of the N-oxides with trimethyl phosphite