Eco-Friendly Synthesis of 2,3-Dihydroquinazolin-4(1H)-ones Catalyzed by FeCl3/Al2O3 and Analysis of Large 1H NMR Diastereotopic Effect

In the present study, we have carried out a condensation reaction for the synthesis of 2,3-dihydroquinazolin-4(1H)-ones from 2-amino-N-benzylbenzamide and different aromatic aldehydes using FeCl3 catalyst supported on Al2O3. It was demonstrated that this material can be used successfully for the nuc...

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Bibliographic Details
Published in:Journal of the Brazilian Chemical Society 2019-01, Vol.30 (1), p.124-131
Main Authors: Monreal, Isabel, Sánchez-Castellanos, Mariano, Ramírez-Gualito, Karla, Cuevas, Gabriel, Espinoza, Karla A., Rivero, Ignacio A.
Format: Article
Language:Portuguese
Subjects:
CHEMISTRY, MULTIDISCIPLINARY
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Summary:In the present study, we have carried out a condensation reaction for the synthesis of 2,3-dihydroquinazolin-4(1H)-ones from 2-amino-N-benzylbenzamide and different aromatic aldehydes using FeCl3 catalyst supported on Al2O3. It was demonstrated that this material can be used successfully for the nucleation of quinazolinones with good to excellent yield; furthermore, the FeCl3/Al2O3 catalyst can be recovered and reused. This catalyst was used before in the synthesis of imidazole with very good yields. The synthesized quinazolinones showed a large range diastereotopic effect over the methylene group and, this anomalous difference was studied through nuclear magnetic resonance (NMR) and computational calculations.
ISSN:1678-4790
DOI:10.21577/0103-5053.20180161