Synthesis of diverse isoxazolylamino-2-(aryl)acetamides using one-pot Multicomponent Reactions: X-ray, Hirshfeld analysis and DFT modeling

Loubidi, Mohammed; Jouha, Jabrane; Hdoufane, Ismail; Hafi, Mohamed El; Tber, Zahira; Cherqaoui, Driss; Mague, Joel T.

doi:10.1016/j.molstruc.2019.127178

Cited by 8 publications

(4 citation statements)

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“…The comprehensive electronic distribution within the Highest Occupied Molecular Orbital (HOMO) and the Lowest Unoccupied Molecular Orbital (LUMO) demonstrates notable similarities involving both elec- tron-donating and electron-withdrawing substituents (depicted in Figure 6). [54][55][56] The energy difference ( ~ELUMO-HOMO ) has been computed and presented in Figure 6 (1.08 eV for electronwithdrawing substituent, 1.59 eV for electron-donating substituent, 3.25 eV for simple benzaldehyde). However, it is noteworthy that the disparity in the HOMO-LUMO energy gap is quite pronounced.…”

Section: Theoretical Aspects Of the Reactionmentioning

confidence: 99%

Bio Inspired CdO Nanoparticles: A Robust and Recyclable Catalyst Towards the Synthesis of Dihydropyrimidone Derivatives via One Pot Three‐Component Coupling Reaction

Bera,

Mahato,

Das

et al. 2024

ChemistrySelect

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An innovative and environmentally sustainable approach is presented for the synthesis of cadmium oxide nanoparticles (CdONPs), leveraging the leaf extract of the pigeon pea plant (Cajanus cajan) as both reductive and capping agents. This environmentally friendly heterogeneous CdONPs was meticulously characterized through FT‐IR, PXRD, HR‐TEM, SEM‐EDAX, XPS and UV‐Vis spectroscopic analyses. These NPs were subsequently applied to facilitate the three‐component Biginelli reaction using ethyl acetoacetate, urea, and substituted benzaldehydes for producing dihydropyrimidone derivatives in good to excellent yield. The methodology was tested for different aldehydes containing electron‐withdrawing and electron‐donating groups. The catalyst demonstrated consistent performance over approximately five cycles, exhibiting negligible loss in yield and catalytic potential. The proposed mechanistic pathway of the reaction was elucidated through intermediate mass analysis and further validated by Density Functional Theory (DFT) calculations and catalytic surface adsorption studies.

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Section: Theoretical Aspects Of the Reactionmentioning

confidence: 99%

Bio Inspired CdO Nanoparticles: A Robust and Recyclable Catalyst Towards the Synthesis of Dihydropyrimidone Derivatives via One Pot Three‐Component Coupling Reaction

Bera,

Mahato,

Das

et al. 2024

ChemistrySelect

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“…There are three points of diversification which means that vast libraries can easily be compiled and in certain cases in drug discovery campaigns, this was accomplished. Both primary and secondary amines, [45][46][47][48][49][50][51] compared to the classical Ugi reaction, give rise to the corresponding α-aminoacylamide, whereas there is a great diversity in the utility of oxocomponent [52][53][54][55] and isocyanide moieties (Figure 6). [45,53,56] The solvent is mostly polar protic (e.g.…”

Section: Scope and Limitationsmentioning

confidence: 99%

“…Brønsted acids as catalysts in the U-3CRs are still under investigation to this day, with Loubidi et al [48] in 2020 reporting perchloric acid (HClO 4 ) U-3CR catalysis towards the synthesis of isoxazoles. The latter are privileged scaffolds, possessing important biological functions.…”

Section: Brønsted Acidsmentioning

confidence: 99%

“…European Journal of Organic Chemistry t-octyl, cyclopentyl and p-methoxyphenyl isocyanide, leading to the formation of U-3CR products 47 in yields 86-96 % with 96-98 % ee. Finally, a gram scale reaction was performed with the selection of benzyl isocyanide, 2-methoxyacetaldehyde and 4-nitroaniline as starting materials to produce an intermediate of (R)-lacosamide (48), an anticonvulsant drug. [105] Application of the protocol led to the desired enantiomeric intermediate 48 with a yield of 90 % and 94 % ee.…”

Section: Eurjocmentioning

confidence: 99%

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The Ugi Three‐Component Reaction; a Valuable Tool in Modern Organic Synthesis

2020

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The Ugi three component reaction (U‐3CR) is a variation of the famous Ugi reaction, discovered almost 60 years ago. Today it is somehow neglected, compared to the classical variation, although the α‐aminoamides, derived from this reaction, have been utilized as inhibitors for various targets and even commercial drugs, offering improved pharmacokinetic properties. In this review, we are describing the scope and limitations of the reaction with a special focus on the developed catalytic protocols, the bioactive compounds, and drugs which are based on the reaction and finally the post modifications that have been reported in order to access drug‐like and privileged scaffolds. A special focus is given to the 3D solid state conformations of the U‐3CR derivatives.

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Investigation of snail shell waste as potential and eco-friendly heterogeneous catalyst for synthesis of 1-(benzothiazolylamino) methyl-2-naphthols derivatives

Benzekri

Sibous

hajri

et al. 2021

Chemical Data Collections

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Synthesis of diverse isoxazolylamino-2-(aryl)acetamides using one-pot Multicomponent Reactions: X-ray, Hirshfeld analysis and DFT modeling

Cited by 8 publications

References 36 publications

Bio Inspired CdO Nanoparticles: A Robust and Recyclable Catalyst Towards the Synthesis of Dihydropyrimidone Derivatives via One Pot Three‐Component Coupling Reaction

Bio Inspired CdO Nanoparticles: A Robust and Recyclable Catalyst Towards the Synthesis of Dihydropyrimidone Derivatives via One Pot Three‐Component Coupling Reaction

The Ugi Three‐Component Reaction; a Valuable Tool in Modern Organic Synthesis

Investigation of snail shell waste as potential and eco-friendly heterogeneous catalyst for synthesis of 1-(benzothiazolylamino) methyl-2-naphthols derivatives

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