Synthesis and reactivity of 3-methylisoxazolo[4,5-c]pyridines

Adembri, G.; Camparini, Alfredo; Ponticelli, Fabio; Tedeschi, Piero

doi:10.1039/p19750002190

Cited by 16 publications

(7 citation statements)

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“…Reaction of 4,6-dichloro-3-methylisoxazolo[4,5-c]pyridine (1) [10] with phloroglucinol in the presence of DBU allowed the preparation of the compounds reported in Scheme 1. Careful selection of both reagent ratio and reaction temperature (Entry a, b or c) allowed isolation of each compound.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Isoxazolopyridobicyclooxacalix[4]arenes: A New Family of Heteracalixarene Systems

et al. 2008

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Section: Resultsmentioning

confidence: 99%

Synthesis of Isoxazolopyridobicyclooxacalix[4]arenes: A New Family of Heteracalixarene Systems

et al. 2008

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“…All reagents were reagent grade and were used without purification. The halo-heteroaryl derivatives 1a, 1b (Donati et al 1991) and 1d (Argibas et al 1992), 1e (Adembri et al 1981), 1f, 1g (Adembri et al 1975), 1h (Camparini et al 1977), were known compounds and were prepared and purified as reported previously. Compound 1c (oil) was prepared from 4-phenyl-3-methylisoxazole following the procedure reported for the synthesis of compounds 1a and 1b.…”

Section: Chemistrymentioning

confidence: 99%

Heteroaryl-susbstituted phenols as potential antioxidants

Ferrini

Fusi

Ponticelli

et al. 2007

Journal of Pharmacy and Pharmacology

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A series of O-heteroaryl phenols have been synthesised and structurally characterised. Photo-Fries rearrangement of these compounds represents a useful way to access the corresponding C-heteroaryl derivatives. The activity of the new phenolic compounds as radical scavengers towards the 2,2'-azino-bis (3-ethylbenzothiazoline-6-sulfonate) (ABTS(+*)) has been evaluated. 2-tert-Butyl-4-(4-phenyl-isoxazol-3-ylmethoxy)-phenol (compound 3c) showed the highest scavenger activity (IC50 value (i.e. the concentration that scavenged 50% of the radicals) 3.17 x 10(-6) M), which was one order of magnitude greater than that of the corresponding lead compound tert-butylhydroxy-anisole (BHA) (IC50 1.04 x 10(-5) M). In further experiments, compound 3c showed dose-dependent inhibition of the oxidation of linoleic acid, as well as methaemoglobin formation, promoted by the presence of the radical generator 2,2'-azobis(amidino-propane) hydrochloride (AAPH) and it was markedly more potent than BHA in these assays.

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“…Also, the C3 position of the resulting compound was reduced to an aromatic methine, a Shapiro [8] and Bamford-Stevens [8,9] reduction product (Scheme 3), instead of a methylene. These questions together with some references, [10] which described the decomposition of N-heteroaryl-N'-tosylhydrazines in basic conditions without studying the mechanism in depth, stimulated our interest in the reaction mechanism.…”

Section: Introductionmentioning

confidence: 98%

Reduction of Different Electron‐Poor N‐Heteroarylhydrazines in Strong Basic Conditions

Unciti‐Broceta

Infantas

Gallo

et al. 2007

Chemistry A European J

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The first application of the Wolff-Kishner reduction methodology to electron-poor heteroaromatic compounds is reported. Hydrazino-containing heterocycles with hydrazone-type tautomery have been reduced under basic conditions. This novel chemistry was successfully applied to mono-dehalogenate a number of electron-poor heterocycles in a regioselective manner. According to the experimental results, this reductive process is a base-catalyzed reaction that takes only place in the presence of air, probably through an oxygen-assisted mechanism. As consequence of the specific features of this kind of hydrazone/enehydrazine tautomers, the overall outcome of the process is the synthesis of a Shapiro-type reduction product by simply using a milder version of the Huang-Minlon methodology.

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Synthesis and reactivity of 3-methylisoxazolo[4,5-c]pyridines

Cited by 16 publications

References 0 publications

Synthesis of Isoxazolopyridobicyclooxacalix[4]arenes: A New Family of Heteracalixarene Systems

Synthesis of Isoxazolopyridobicyclooxacalix[4]arenes: A New Family of Heteracalixarene Systems

Heteroaryl-susbstituted phenols as potential antioxidants

Reduction of Different Electron‐Poor N‐Heteroarylhydrazines in Strong Basic Conditions

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