Direct synthesis of oxazolidin-2-ones from tert -butyl allylcarbamate via halo-induced cyclisation
| Autor: | Paitoon Rashatasakhon, Waroton Paisuwan, Mongkol Sukwattanasinitt, Anawat Ajavakom, Thanakrit Chantra |
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| Rok vydání: | 2017 |
| Předmět: |
Tert butyl
Reaction conditions 010405 organic chemistry Chemistry Aryl Organic Chemistry 010402 general chemistry 01 natural sciences Biochemistry Combinatorial chemistry 0104 chemical sciences Toloxatone Para position chemistry.chemical_compound Reagent Drug Discovery Halogen medicine Organic chemistry medicine.drug |
| Zdroj: | Tetrahedron. 73:3363-3367 |
| ISSN: | 0040-4020 |
| Popis: | A novel synthetic pathway towards the 2-oxazolidinone derivatives involving the halo-induced cyclisation of tert-butyl allyl(phenyl)carbamate was successfully developed. Various halogenating reagents were evaluated under different reaction conditions for the reaction optimisation. Interestingly, the synthetic route to 2-oxazolidinone derivatives containing one halogen atom in the aliphatic site or two halogen atoms including the extra halogen atom substituted in the aryl group at the para position, were thoroughly established for all chloro-, bromo- and iodo compounds. Either halo-unsubstituted-aryl oxazolidinone or p-halo-substituted-aryl oxazolidinone could be selectively produced by selecting the appropriate choices of halogenated reagents and reaction conditions e.g. reaction time and temperature. Toloxatone, a commercial antidepressant, was successfully synthesized by using this developed method. |
| Databáze: | OpenAIRE |
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