58144-66-4Relevant academic research and scientific papers
Synthesis of 3-Acyl-Isoxazoles via Radical 5-endo trig Cyclization of β,γ-Unsaturated Ketones with NaNO2
Chen, Dengfeng,Huang, Shenlin,Jiang, Ping,Wang, Yaming,Zheng, Yu
supporting information, (2022/02/07)
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
Development of variously functionalized nitrile oxides
Asahara, Haruyasu,Arikiyo, Keita,Nishiwaki, Nagatoshi
, p. 1241 - 1245 (2015/08/18)
N-Methylated amides (N,4-dimethylbenzamide and N-methylcyclohexanecarboxamide) were systematically subjected to chemical transformations, namely, N-tosylation followed by nucleophilic substitution. The amide function was converted to the corresponding carboxylic acid, esters, amides, aldehyde, and ketone upon treatment with hydroxide, alkoxide, amine, diisobutylaluminium hydride and Grignard reagent, respectively. In these transformations, N-methyl-N-tosylcarboxamides behave like a Weinreb amide. Similarly, N-methyl-5-phenylisoxazole-3-carboxamide was converted into 3-functionalized isoxazole derivatives. Since the amide was prepared by the cycloaddition reaction of ethynylbenzene and N-methylcarbamoylnitrile oxide, the nitrile oxide served as the equivalent of the nitrile oxides bearing a variety of functional groups such as carboxy, alkoxycarbonyl, carbamoyl, acyl and formyl moieties.
Effect of aqueous polyethylene glycol on 1,3-dipolar cycloaddition of benzoylnitromethane/ethyl 2-nitroacetate with dipolarophiles: Green synthesis of isoxazoles and isoxazolines
Chary, R. Gangadhara,Reddy, G. Rajeshwar,Ganesh,Prasad, K. Vara,Raghunadh, Akula,Krishna,Mukherjee, Soumita,Pal, Manojit
supporting information, p. 160 - 164 (2014/03/21)
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
Synthesis of tetrafunctionalized 2-azido-3-hydroxy-1,4-diones and their transformation into 5-substituted 3-acylisoxazoles
Juhasz-Totha, Eva,Patonay, Tamas
, p. 3055 - 3064 (2007/10/03)
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.
