Control of selectivity in the preparation of 2-substituted benzoazoles by adjusting the surface hydrophobicity in two solid-based sulfonic acid catalysts.
Org Biomol Chem
; 21(8): 1692-1703, 2023 Feb 22.
Article
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| MEDLINE
| ID: mdl-36734617
ABSTRACT
A series of metal-free tandem reactions for the synthesis of pharmaceutically important 2-substituted benzoazoles from isothiocyanates and 2-aminothiophenol under catalyst-free conditions in the presence of Et-PMO-Me-PrSO3H (1a) and SBA-15-PrSO3H (1b) as solid acids were carried out in a highly selective way under solvent free conditions. A significant selectivity changeover toward either 2-mercaptobenzoxazole or 2-aminobenzoazole derivatives could be achieved by changing the employed catalyst from the relatively hydrophobic material 1a to the more hydrophilic catalyst 1b. This simple experimental procedure with a novel selective approach toward benzoazoles accompanied by green and reusable catalysts could be considered as an alternative to the existing methods for the synthesis of 2-substituted benzoazole derivatives.
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MEDLINE
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En
Revista:
Org Biomol Chem
Asunto de la revista:
BIOQUIMICA
/
QUIMICA
Año:
2023
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Article
País de afiliación:
Irán