Tehami, Maryam and Imam, Hasan Tanvir and Abdullah, Iskandar and Hosford, Joseph and Wong, Xiao Juie and Rahman, Noorsaadah Abd and Wong, Lu Shin (2024) Biocatalytic Generation of o-Quinone Imines in the Synthesis of 1,4-Benzoxazines and Its Comparative Green Chemistry Metrics. ACS Sustainable Chemistry & Engineering, 12 (7). pp. 2678-2685. ISSN 2168-0485, DOI https://doi.org/10.1021/acssuschemeng.3c06758.
Full text not available from this repository.Abstract
1,4-Benzoxazines are important motifs in many pharmaceuticals and can be formed by a reaction sequence involving the oxidation of o-aminophenols to their corresponding quinone imine followed by an in situ inverse electron demand Diels-Alder (IEDDA) cycloaddition with a suitable dienophile. Reported herein is the development of a reaction sequence that employs horseradish peroxidase to catalyze the oxidation of the aminophenols prior to the IEDDA as a more sustainable alternative to the use of conventional stoichiometric oxidants. The synthesis of 10 example benzoxazines is demonstrated in this ``one-pot, two-step'' procedure with yields between 42% and 92%. The green chemistry metrics, including the E-factor and generalized reaction mass efficiency, for this biocatalytic reaction were compared against the conventional chemical approach. It was found that the reported biocatalytic route was approximately twice as green by these measures.
| Item Type: | Article |
|---|---|
| Funders: | The British Council in India (172701477); (EP/K011685/1); (EP/P510889/1); (EP/J50032X/1), UK Research & Innovation (UKRI) Engineering & Physical Sciences Research Council (EPSRC) (BB/M011208/1), UK Research & Innovation (UKRI) Biotechnology and Biological Sciences Research Council (BBSRC) |
| Uncontrolled Keywords: | peroxidase; horseradish peroxidase; Diels-Alderreaction; inverse electron demand Diels-Alder; E-factor; reaction mass efficiency; tandem reaction |
| Subjects: | Q Science > Q Science (General) Q Science > QD Chemistry |
| Divisions: | Faculty of Science > Department of Chemistry Institute of Advanced Studies |
| Depositing User: | Ms. Juhaida Abd Rahim |
| Date Deposited: | 08 Nov 2024 04:37 |
| Last Modified: | 08 Nov 2024 04:37 |
| URI: | http://eprints.um.edu.my/id/eprint/45667 |
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