Primary nitro compounds: progress in the synthesis of isoxazoles by condensation with aldehydes or activated ketones

De Sarlo, Francesco; Machetti, Fabrizio

doi:10.1039/d3ob00960b

Cited by 4 publications

(2 citation statements)

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“…On the other hand, the use of the β‐nitroenone 11 led to a complex mixture of compounds from which it was possible to isolate the isoxazole 14 (37 % of yield), obtained via dinitro compound 13 (Scheme 1). [24] …”

Section: Resultsmentioning

confidence: 99%

Investigations on the Use of Deep Eutectic Solvents (DESs) as Promoters for the Conjugate Addition of α‐Nitroketones to Electron‐Poor Alkenes

Gentili,

Marcantoni,

Tiecco

et al. 2024

ChemistrySelect

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DESs were profitably investigated as solvents and promoters of the conjugate reaction addition of cyclic and acyclic α‐nitroketones to a variety of electron‐poor alkenes. The best results were obtained conducing the reaction in betaine:1,2‐propanediol (1 : 5 molar ratio) DES at room temperature, and enones were demonstrated to be the most effective Michael acceptors. The same reaction conducted by using different molar ratios of the components in this DES showed the eutectic point to be the most effective in terms of the yields observed.

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Section: Resultsmentioning

confidence: 99%

Investigations on the Use of Deep Eutectic Solvents (DESs) as Promoters for the Conjugate Addition of α‐Nitroketones to Electron‐Poor Alkenes

Gentili,

Marcantoni,

Tiecco

et al. 2024

ChemistrySelect

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“…A major contribution to the acidity is due to C-H bond geminal to the nitro group [ 3 ]. Generation of carbanions is a fundamental step in organic synthesis, and the nitro group is widely used to such purpose [ 4 , 5 , 6 ]. The heterolytic cleavage of activated C-H bonds has been investigated for a long time [ 7 ], in particular for nitro compounds, where the so-called “nitroalkane anomaly” was immediately recognized and related to solvent effects [ 8 ].…”

Section: Introductionmentioning

confidence: 99%

Probing Reactivity with External Forces: The Case of Nitroacetamides in Water

La Penna,

Machetti

2023

Molecules

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Many computational methods have been applied to interpret and predict changes in reactivity by slight modifications of a given molecular scaffold. We describe a novel and simple method based on approximate density-functional theory of valence electrons that can be applied within a large high-performance computational infrastructure to probe such changes using a statistical sample of molecular configurations, including the solvent. All the used computational tools are fully open-source. Following our previous application, we are able to explain the high acidity of C-H bond at α position in nitro compounds when the amide linkage an ammonium group is inserted into the α substituent.

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Access to Isoxazoles via Photo-oxygenation of Furan Tethered α-Azidoketones

Newar,

Kumar,

Borah

et al. 2024

J. Org. Chem.

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Photocatalyst-free visible light-enabled direct oxygenation of furan-tethered α-azidoketones was studied. The reaction yielded various products depending on the substituents, with isoxazoles forming as the major products. The findings suggest that singlet oxygen was generated during the reaction and reacted with α-azidoketones in a [4 + 2] fashion to yield endoperoxides, which rearranged in multiple ways to generate isoxazoles. Some of the synthesized isoxazoles were evaluated as αglucosidase inhibitors, and three of them 5bi, 5bj, and 5bl exhibited good activity with IC 50

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Primary nitro compounds: progress in the synthesis of isoxazoles by condensation with aldehydes or activated ketones

Abstract: Among known strategies directed to the synthesis of isoxazole derivatives reactions of aldehydes with primary nitro compounds deserve a comprehensive treatment, including the historical development as well as the more...

Cited by 4 publications

References 100 publications

Investigations on the Use of Deep Eutectic Solvents (DESs) as Promoters for the Conjugate Addition of α‐Nitroketones to Electron‐Poor Alkenes

Investigations on the Use of Deep Eutectic Solvents (DESs) as Promoters for the Conjugate Addition of α‐Nitroketones to Electron‐Poor Alkenes

Probing Reactivity with External Forces: The Case of Nitroacetamides in Water

Access to Isoxazoles via Photo-oxygenation of Furan Tethered α-Azidoketones

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