Abstract
β-Hydroxynitriles are essential intermediates in the synthesis of diverse bioactive compounds and clinical drugs. One of the precursor reactions to these intermediates is the opening of an epoxide ring with a cyanide nucleophile. In the present study, we report a milder and safer route to β-hydroxynitriles employing recyclable, Amberlyst A-21 resin in the ring-opening of epoxides with acetone cyanohydrin in water. A diverse range of substrates (fifteen), including aromatic epoxides, phenoxy epoxides, non-terminal, and terminal aliphatic epoxides, are investigated under the optimized conditions to afford the desired β-hydroxynitriles in good to excellent yield. In addition to this, the recyclability of the Amberlyst A-21 resin is also successfully demonstrated. This relatively safer methodology has the potential to be explored in other organic transformations.
Original language | English |
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Pages (from-to) | 8200-8208 |
Number of pages | 9 |
Journal | Arabian Journal of Chemistry |
Volume | 13 |
Issue number | 11 |
DOIs | |
Publication status | Published - Nov 2020 |
Keywords
- Acetone cyanohydrin
- Amberlyst A-21
- Epoxide opening
- Water
- β-Hydroxynitriles
ASJC Scopus subject areas
- General Chemistry
- General Chemical Engineering