Synthesis of 2,2-diphenyl-1,3,2-oxazaborolidin-5-one promoted by montmorillonite and microwaves: A green approach methodology

Studies have shown that the heterocyclic molecules of the 2,2-diphenyl-1,3,2-oxazaborolidin-5-one (DPOXA) type have wide and varied biological activity with herbicidal, insecticidal, fungicidal, antibacterial, and apoptotic properties. Several methods are reported for synthesizing this type of molecule, but they require strong acid conditions to release phenylboronic acid, the residues of which impact the environment. The method of synthesis proposed in this study uses montmorillonite (TAFF), microwave irradiation, and an eight α-amino acid. The transformation percentages evaluated by UHPLC-MS/MS, and generated from the optimal conditions of power (W), temperature (°C,) and the amount of TAFF (mg), reflect excellent yields ranging from 81-96 %, in a reaction time of 5 min under solvent-free conditions. Findings allow us to confirm that this methodology is adequate for synthesizing this type of molecule, which has shown significant biological activity.

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Journal
Results in Chemistry
Published
2024-09-06
DOI
https://doi.org/10.1016/j.rechem.2024.101771
Primary Topic
Synthesis and biological activity
Type
article
Field-Weighted Citation Impact
0.00

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article

Synthesis of 2,2-diphenyl-1,3,2-oxazaborolidin-5-one promoted by montmorillonite and microwaves: A green approach methodology

Raquel Gómez‐Pliego, Anuar Gómez‐Tagle, Benjamín Velasco‐Bejarano, Alan Álvarez‐Sánchez et al.
Results in Chemistry
Synthesis and biological activity
article

Synthesis of 2,2-diphenyl-1,3,2-oxazaborolidin-5-one promoted by montmorillonite and microwaves: A green approach methodology

Raquel Gómez‐Pliego, Anuar Gómez‐Tagle, Benjamín Velasco‐Bejarano, Alan Álvarez‐Sánchez, Rodrigo González-Castañeda, Omar Negrellos Correa
article en

Abstract

Studies have shown that the heterocyclic molecules of the 2,2-diphenyl-1,3,2-oxazaborolidin-5-one (DPOXA) type have wide and varied biological activity with herbicidal, insecticidal, fungicidal, antibacterial, and apoptotic properties. Several methods are reported for synthesizing this type of molecule, but they require strong acid conditions to release phenylboronic acid, the residues of which impact the environment. The method of synthesis proposed in this study uses montmorillonite (TAFF), microwave irradiation, and an eight α-amino acid. The transformation percentages evaluated by UHPLC-MS/MS, and generated from the optimal conditions of power (W), temperature (°C,) and the amount of TAFF (mg), reflect excellent yields ranging from 81-96 %, in a reaction time of 5 min under solvent-free conditions. Findings allow us to confirm that this methodology is adequate for synthesizing this type of molecule, which has shown significant biological activity.

Results in ChemistryVol. 11
Universidad de Cuautitlán Izcalli (MX), Rede de Química e Tecnologia (PT)
Dirección General de Asuntos del Personal Académico, Universidad Nacional Autónoma de México
Openalex Percentile: Top 89%
Synthesis and biological activity
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