58144-64-2

Upstream product

• 33108-89-3 N-hydroxy-2-oxo-2-p-tolyl-acetimidoyl chloride 
• 20913-05-7 (Benzoylmethylene)triphenylphosphorane 
• 78189-50-1 5-phenylisoxazole-3-carboxylic acid chloride 
• 108-88-3 toluene 
• 14441-90-8 5-phenyl-3-isoxazolecarboxylic acid 
• 852211-39-3 4-(4-methylphenyl)-1-phenylbut-3-yn-1-ol 
• 536-74-3 phenylacetylene 
• 122-00-9 para-methylacetophenone 

Downstream Products

• 1431970-95-4 C₂₈H₂₁N₃O₄ 
• 1431970-84-1 C₂₇H₁₉N₃O₄ 
• 1431971-05-9 C₂₁H₁₃Cl₂N₃O₃S 
• 1431971-14-0 C₁₇H₁₄N₂O₂ 

Relevant academic research and scientific papers

Synthesis of 3-Acyl-Isoxazoles via Radical 5-endo trig Cyclization of β,γ-Unsaturated Ketones with NaNO2

Here we report a facile cyclization reaction of β,γ-unsaturated ketones with NaNO2 under mild conditions to construct 3-acyl-isoxazoles. This transformation is realized via nitrosation of the activated methylene, radical 5-endo trig cyclization

Facile synthesis of disubstituted isoxazoles from homopropargylic alcohol via C=N bond formation

A novel iron-catalyzed aerobic oxidative reaction to synthesize disubstituted isoxazoles from homopropargylic alcohol, t-BuONO, and H2O is developed. The method provides mild conditions to afford a variety of useful substituted heterocycles in an efficient and regioselective manner. The mechanism has been studied and proposed, which indicates that the transformation can be realized through construction of a C=N bond and C=O bond, C-H oxidation, and then cyclization. Moreover, this method can be enlarged to gram scale.

Synthesis of functionally substituted isoxazole and isothiazole derivatives

Acylation of benzene and toluene with 5-phenyl- and 5-(p-tolyl)isoxazole-3- carbonyl chlorides gave 5-phenyl(or p-tolyl)isoxazol-3-yl phenyl(or p-tolyl)ketones which were reduced to the corresponding alcohols with sodium tetrahydridoborate in propan-2-ol. Selective reduction of the carboxy group in 4,5-dichloroisothiazole-3-carboxylic acid was achieved by the action of BH 3, and the aldehyde group in 4-formyl-2-methoxyphenyl 5-arylisoxazole-3-carboxylates and 4,5-dichloroisothiazole-3-carboxylates was reduced to hydroxymethyl group with sodium triacetoxyhydridoborate in benzene. Acylation of the resulting hydroxymethyl derivatives with 5-arylisoxazole- and 4,5-dichloroisothiazole-3-carbonyl chlorides afforded the corresponding esters containing two azole fragments in their molecules.