58144-67-5

Upstream product

• 6305-05-1 2-(4-chlorophenyl)-N-hydroxy-2-oxoethanimidoyl chloride 
• 20913-05-7 (Benzoylmethylene)triphenylphosphorane 
• 5468-33-7 1-(4-chlorophenyl)-2-nitroethan-1-one 
• 536-74-3 phenylacetylene 
• 99-91-2 para-chloroacetophenone 
• 1638618-21-9 4-(4-chlorophenyl)-1-phenylbut-3-yn-1-ol 

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

Does electrophilic activation of nitroalkanes in polyphosphoric acid involve formation of nitrile oxides?

The mechanistic rationale involving activation of nitroalkanes towards interaction with nucleophilic reagents in the presence of polyphosphoric acid (PPA) was re-evaluated. Could nitrile oxide moieties be formed during this process? This experiment demonstrates that at least in some cases this could happen, as generated nitrile oxides were successfully intercepted as adducts of [3 + 2] cycloadditions. This journal is

Effect of aqueous polyethylene glycol on 1,3-dipolar cycloaddition of benzoylnitromethane/ethyl 2-nitroacetate with dipolarophiles: Green synthesis of isoxazoles and isoxazolines

A 1:1 mixture of water-polyethylene glycol (PEG) facilitated the 1,3-dipolar cycloaddition of benzoylnitromethane/ethyl 2-nitroacetate with terminal alkynes or alkenes leading to isoxazoles or isoxazolines under green conditions. The methodology is free f

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 tetrafunctionalized 2-azido-3-hydroxy-1,4-diones and their transformation into 5-substituted 3-acylisoxazoles

An efficient synthesis of 2-azido-3-hydroxy-1,4-diones, based on the base-induced coupling of α-azido ketones and α-oxo aldehydes, has been developed. The coupling reaction took place with moderate to good diastereoselectivity. The relative configurations of the adducts have been determined by X-ray analysis. Treatment of tetrafunctionalized synthons 2-azido-3-hydroxy-1,4-diones with mesyl chloride in the presence of base afforded 5-substituted 3-acylisoxazoles, through 2-azido-2-alkene-1,4-dione intermediates. Analogous treatment of α-azido ketones with α-oxo esters resulted in the formation of the unstable 3-azido-2-hydroxy-4-oxobut-anoates. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.