Synthesis of isoxazolo[4,5-b]pyridine derivatives (microreview)

Nikol’skiy, Vladislav V.; Старосотников, А. М.

doi:10.1007/s10593-023-03186-y

Cited by 3 publications

(3 citation statements)

References 11 publications

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“…reactions of 4-amino-5-benzoylisoxazoles with ketones or 1,3dicarbonyl compounds [10,13]. These and some additional examples of isoxazolo [4,5-b]pyridine core synthesis have been summarized in a microreview [22].…”

Section: Introductionmentioning

confidence: 99%

“…Alternatively ( Scheme 1B ), isoxazolo[4,5- b ]pyridines can be constructed via intramolecular cyclization of 4-(propargylamino)isoxazoles [ 21 ] or through reactions of 4-amino-5-benzoylisoxazoles with ketones or 1,3-dicarbonyl compounds [ 10 , 13 ]. These and some additional examples of isoxazolo[4,5- b ]pyridine core synthesis have been summarized in a microreview [ 22 ].…”

Section: Introductionmentioning

confidence: 99%

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Mild and efficient synthesis and base-promoted rearrangement of novel isoxazolo[4,5-b]pyridines

Nikol’skiy,

Minyaev,

Bastrakov

et al. 2024

Beilstein J. Org. Chem.

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An efficient method for the synthesis of isoxazolo[4,5-b]pyridines has been developed on the basis of readily available 2-chloro-3-nitropyridines via the intramolecular nucleophilic substitution of the nitro group as a key step. The previously unknown base-promoted Boulton–Katritzky rearrangement of isoxazolo[4,5-b]pyridine-3-carbaldehyde arylhydrazones into 3-hydroxy-2-(2-aryl[1,2,3]triazol-4-yl)pyridines was observed.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Mild and efficient synthesis and base-promoted rearrangement of novel isoxazolo[4,5-b]pyridines

Nikol’skiy,

Minyaev,

Bastrakov

et al. 2024

Beilstein J. Org. Chem.

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“…Isoxazole ring, as well as its hydrogenated analogs (isoxazolines and isoxazolidines), are key molecular segments of many important bioactive structures such as afoxolaner [1], lotilaner [2], sarolaner [3], fenoxasulfone [4], and many others [5][6][7][8][9]. The most universal strategy for the preparation of five-membered heterocycles (including isoxazoles) is [3+2] cycloaddition (32CA) [10][11][12].…”

Section: Introductionmentioning

confidence: 99%

Energetic Aspects and Molecular Mechanism of 3-Nitro-substituted 2-Isoxazolines Formation via Nitrile N-Oxide [3+2] Cycloaddition: An MEDT Computational Study

Dresler,

Wróblewska,

Jasiński

2024

Molecules

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Regioselectivity and the molecular mechanism of the [3+2] cycloaddition reaction between nitro-substituted formonitrile N-oxide 1 and electron-rich alkenes were explored on the basis of the wb97xd/6-311+G(d) (PCM) quantum chemical calculations. It was established that the thermodynamic factors allow for the formation of stable cycloadducts along all considered models. The analysis of the kinetic parameters of the main processes show that all [3+2] cycloadditions should be realized with full regioselectivity. In all cases, the formation of 5-substituted 3-nitro-2-isoxazolidines is clearly preferred. It is interesting that regiodirection is not determined by the local electrophile/nucleophile interactions but by steric effects. From a mechanistic point of view, all considered reactions should be treated as polar, one-step reactions. All attempts to locate the hypothetical zwitterionic intermediates along the cycloaddition paths were, however, not successful.

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Divergent Synthesis of Isoxazolo[5,4‐b]pyridines

Li,

Huang

et al. 2024

Eur J Org Chem

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Isoxazolopyridines are highly significant for the development of pharmaceutics and new materials. In continuation of our ongoing research on transformations of 5‐aminoisoxazoles, herein we report a divergent synthesis of two kinds of novel isoxazolo[5,4‐b]pyridines via condensation of 5‐aminoisoxazoles with β,γ‐alkynyl‐α‐imino esters. By using two different silver salts and a phosphoric acid as catalysts, isoxazolo[5,4‐b]pyridine‐α‐carboxylates and isoxazolo[5,4‐b]pyridine‐γ‐carboxylates were constructed as major isomers in moderate to good yields respectively. The structures of the two kinds of the isoxazolo[5,4‐b]pyridines were confirmed by X‐ray crystal structural analyses. Furhermore, control experiments were conducted to elucidate the reaction mechanism.

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Synthesis of isoxazolo[4,5-b]pyridine derivatives (microreview)

Cited by 3 publications

References 11 publications

Mild and efficient synthesis and base-promoted rearrangement of novel isoxazolo[4,5-b]pyridines

Mild and efficient synthesis and base-promoted rearrangement of novel isoxazolo[4,5-b]pyridines

Energetic Aspects and Molecular Mechanism of 3-Nitro-substituted 2-Isoxazolines Formation via Nitrile N-Oxide [3+2] Cycloaddition: An MEDT Computational Study

Divergent Synthesis of Isoxazolo[5,4‐b]pyridines

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