57354-90-2

Upstream product

• 127-09-3 sodium acetate 
• 108-24-7 acetic anhydride 
• 932-90-1 Benzaldoxime 
• 27975-80-0 (+/-)-3-bromo-1-phenyl-1-butyne 
• 122-57-6 1-Phenylbut-1-en-3-one 
• 698-16-8 benzohydroximoyl chloride 
• 84679-59-4 methyl 4-nitro-3-phenylisoxazole-5-carboxylate 
• 7647-01-0 hydrogenchloride 
• 113639-41-1 4-Iodo-5-methyl-4-nitro-3-phenyl-4,5-dihydro-isoxazole 
• 186581-53-3 diazomethane 
• 31301-41-4 4-nitro-3-phenylisoxazole 
• 10230-68-9 1-nitro-2-propanone 
• 1008-74-8 5-methyl-3-phenylisoxazole 

Downstream Products

• 14838-25-6 4-nitro-3-phenyl-5-styrylisoxazole 
• 58311-79-8 3-methyl-4-nitro-5-phenyl-1⁽²⁾H-pyrazole 
• 21169-65-3 5-methyl-3-phenyl-1,2-oxazole-4-amine 
• 21205-24-3 ω-nitroacetophenone oxime 
• 14733-92-7 N-(3-phenyl-5-styryl-isoxazol-4-yl)-acetamide 
• 14733-91-6 3-phenyl-5-styryl-isoxazol-4-ylamine 
• 112884-51-2 3-methyl-5-phenyl-1⁽²⁾H-pyrazol-4-ylamine 
• 13054-64-3 5-methyl-3-phenyl-isoxazol-4-ol 
• 14838-25-6 4-nitro-3-phenyl-5-styryl-isoxazole 

Relevant academic research and scientific papers

Synthesis of 4-Nitroisoxazoles via NO/NO2 -Mediated Heterocyclization of Aryl-Substituted α,β-Unsaturated Ketones

A straightforward approach for the synthesis of 4-nitroisoxazoles has been developed via heterocyclization of aryl/hetaryl-substituted α,β-unsaturated ketones upon treatment with tetranitromethane-triethylamine (TNM-TEA) complex or t -BuONO. This strategy features high efficiency and wide substrate tolerance under simple reaction conditions.

Enantioselective Cyclopropanation of 4-Nitroisoxazole Derivatives

The present study reports an asymmetric organocatalytic cascade reaction of 4-nitroisoxazole derivative with α,β-unsaturated aldehydes catalysed by chiral secondary amine. Using this approach, 1,2,3-trisubstituted cyclopropane products were obtained in isolated yields up to 98% with moderate diastereoselectivities, and enantiopurity up to 99% ee. Moreover, this synthetic protocol can be used for further applications, as shown by a set of additional transformations of the corresponding cyclopropanes and by the formal synthesis of GABA ligands. (Figure presented.).

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.

DIRECT FIVE-MEMBERED HETEROANNULATION REACTIONS FOR THE ISOXAZOLE SYSTEM BY 1,3-DIPOLAR CYCLOADDITIONS ON 5-UNSUBSTITUTED 4-NITRO DERIVATIVES: SYNTHESIS OF PYRAZOLO- AND PYRROLOISOXAZOLES

One-step syntheses of aromatic derivatives of the title binuclear systems have been achieved by reaction of compound 3b with diazomethane, as well as by treatment of 3a and 3b with diphenylnitrilimine and 3-methyl-2,4-diphenyloxazolium 5-oxide, respective

Transformations in the isoxazole series: Synthesis of substituted 2-aminothiazoles

Substitued N-(isoxazol-4-yl)thioureas 1 undergo a transformation in the presence of hexacarbonylmolybdenum and acid to yield functionalized thiazoles 3 in a one-pot reaction. In a few cases, 1,4,5-trisubstituted dihydroimidazoleth, iones 4 are also isolated as side products. Mechanistic considerations are outlined and scope and limitations of this new methodology discussed.

SYNTHESIS AND PROPERTIES OF 4-HALO-4-NITROISOXAZOLINES

Chloro-, bromo-, and iodo-derivatives of substituted 4-nitroisoxazolines have been synthesized by direct halogenation of the latter, and their chemical properties have been studied, among them their conversion to 4-nitroisoxazole derivatives by eliminatio