Journal
GREEN CHEMISTRY
Volume 24, Issue 11, Pages 4628-4633Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d2gc00503d
Keywords
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Funding
- CERCA Program/Generalitat de Catalunya, ICREA, MINECO/FEDER [PID2020-112684GB-100, PID2019-109236RB-I00]
- MICINN through Severo Ochoa Excellence Accreditation [CEX2019-000925-S]
- AGAUR [2017-SGR-232, 2017-SGR-1139]
- La Caixa Foundation [100010434]
- Predoctoral Fellowship - EU [LCF/BQ/IN18/11660003, 713673]
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The article presents an efficient synthesis method using TBD catalyst to convert epoxy amines to 2-oxazolidone, combining the use of CO2 as a C-1 source and halide-free organocatalysis to continuously synthesize a series of heterocyclic products over a two-week period.
A polystyrene-supported 1,5,7-triazabicyclodec-5-ene (TBD) was used as a highly recyclable and stable catalyst for the conversion of epoxy amines into various 2-oxazolidone scaffolds. This approach combines the use of CO2 as an attractive, cheap and abundant C-1 source with a halide-free, organocatalytic continuous flow approach to promote the efficient synthesis of a small library of pharmaceutically relevant 2-substituted oxazolidinones, including the known drug Toloxatone. A packed bed reactor containing the same batch of immobilized catalyst could be applied for the continuous synthesis of a series of heterocyclic products over a two week period without significant changes in catalytic activity.
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