Category: 144537-05-3

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A nitrile oxide containing a carbamoyl group is readily generated upon the treatment of 2-methyl-4-nitro-3-isoxazolin-5(2H)-one with water under mild reaction conditions, even in the absence of special reagents. The obtained nitrile oxide undergoes cycloaddition with dipolarophiles, alkynes and alkenes, to afford the corresponding isoxazol(in)es, which are useful intermediates in the synthesis of polyfunctionalized compounds. A plausible mechanism underlying the formation of the nitrile oxide is proposed, which involves an anomalous hydration/dehydration sequence. DFT calculations were also performed to support this mechanism.

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Reference：
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem

September 13,2021 News Awesome Chemistry Experiments For 144537-05-3

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1,4-Diazabicyclo[2.2.2]octane (DABCO) or other suitable N-bases cause primary activated nitro compounds to condense with alkenes to yield isoxazolines or with alkynes to give isoxazoles. As the molar ratio of the base with respect to the dipolarophile decreased, the reaction became slower, but the nitro compound became more resistant to hydrolytic cleavage. The best results were achieved with a molar ratio of base in the range of 0.05-0.1. The reactions were carried out in chloroform at 60C; for ethyl nitroacetate and phenylnitromethane, ethanol at 80C can be employed with better results and shorter reaction times. A catalytic cycle is proposed: in chloroform the hydrogen-bonded ion pair formed between the nitronate and the protonated base undergoes reversible cycloaddition with the dipolarophile and then the hydrogen-bonded intermediate adduct releases water by reaction with a second nitro molecule to give the product and the hydrogen-bonded nitronate. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.

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Reference：
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem

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A new series of 5-phenyl-3-isoxazole carboxamides (4a-j) have been synthesized by reacting 5-phenyl-3-isoxazole carboxylate with various amines. All the synthesized compounds were characterized by their analytical and spectral data. These compounds were-evaluated for antimicrobial activity against S. aureus and E. coli using disc diffusion method where few of them showed significant antibacterial activity.

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Reference：
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem

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Gentle generation of nitrile oxide bearing a carbamoyl group was performed. 4-Nitro-3-isoxazolin-5-one was treated with dipolarophiles in the mixed solvent (MeCN/H2O) at room temperature to afford cycloadducts in good yields.

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Reference：
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem

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2-Methyl-4-nitro-5(2H)-isoxazolone (1) was found to be a versatile precursor for a functionalized nitrile oxide by reaction with dipolarophiles giving 3-(N-methylcarbamoyl)isoxazole (2 or 3) derivatives.

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Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem

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A series of new 3-(aminomethyl)pyrazoles and 3-(aminomethyl)isoxazoles was synthesized along a route involving the formation as key intermediates of esters of 5-substituted 1H-pyrazole-3-carboxylic and 1H-isoxazole-3-carboxylic acids. All compounds obtained were characterized by physicochemical constants, IR, 1H, 13C NMR, and mass spectra.

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Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem

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1,4-Diazabicyclo[2.2.2]octane (DABCO) as an efficient reagent for the synthesis of isoxazole derivatives from primary nitro compounds and dipolarophiles: The role of the base

The dehydration of primary nitro compounds can be performed by bases in the presence of dipolarophiles. The reactivity of several tertiary amines or azaheteroaromatic compounds containing one or two basic centres is shown to be related to the ability of the protonated base to establish H-bonded ion pairs with the adduct that is formed from the nitronate and the dipolarophile in chloroform. Among the organic bases examined, caged tertiary diamine 1,4-diazabicyclo[2.2.2]octane (DABCO) gave the best results. The reaction is applicable to activated nitro compounds and to phenylnitromethane and affords isoxazoline derivatives in higher yields compared with those of other methods. The reaction, however, is not compatible with nitroalkanes. The proposed mechanism of the reaction is based on the collapse of the H-bonded ion pair. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.

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Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem

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Development of variously functionalized nitrile oxides

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.

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Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem

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METHODS OF MODULATING CFTR ACTIVITY

The invention encompasses methods of modulating CFTR activity in a subject in need thereof comprising administering an effective amount of a compound of Formula (I). The invention also encompasses methods of treating a condition associated with CFTR activity or condition associated with a dysfunction of proteostasis comprising administering to a subject an effective amount of a compound of Formula (I).

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Isoxazole – Wikipedia,
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Competitive Copper Catalysis in the Condensation of Primary Nitro Compounds with Terminal Alkynes: Synthesis of Isoxazoles

Isoxazoles, mainly 3,5-disubstituted, are prepared by catalytic condensation of primary nitro compounds with terminal acetylenes by using a copper/base catalytic system. The additional catalytic effect of the copper(II) salts is evidenced by comparing the kinetic profiles. Selectivity dependence on reaction conditions is considered for phenylacetylene in the following competitive processes: oxidative coupling of terminal alkynes to conjugated diynes catalyzed by CuIIand base in the presence of air; production of furazans beside condensation with benzoylnitromethane to 3-benzoylisoxazoles, as a result of the reaction of the dipolarophile with 3,4-dibenzoylfuroxan; addition of electron-poor alkynes (e.g., methyl propiolate) with themselves and with the nitro compound. Thus, oxidative coupling is negligible in reactions with ?active? nitro compounds, whereas with nitroalkanes both products are observed: only trace amounts of isoxazoles are detected without copper. Similarly, in the presence of copper, 3-benzoyl-5-phenylisoxazole is predominant over the furazan. Furthermore, condensations of electron-poor alkynes give complex reaction mixtures in the presence of base alone, but cycloadducts are conveniently prepared with copper. The results indicate the practical and general utility of this catalytic method for synthetic practice.

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Reference£º
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem