S,S-Dimethyl Dithiocarbonate as a Valuable Starting Material for the Synthesis of 5-Substituted Oxazolidinones Under Solid-Liquid Phase Transfer Catalysis (SL-PTC) Conditions

Dario      Landini; Matteo      Salsa; Gianni      Carvoli; Ilir      Pecnikaj

doi:10.2174/157017806779117111

Abstract

N-Alkyl and N-aryl 5-substituted oxazolidinones 12-19 were prepared in good to excellent yields by reaction of N-alkyl and N-aryl 1,2-amino alcohols 3-10 with S,S-dimethyldithiocarbonate (11) in the presence of solid NaOH under SL-PTC conditions. The procedure is particularly suitable for scale-up the process involving the use of cheap and ecosafe reagents under mild reaction conditions.

Keywords: S,S-dimethyldithiocarbonate, 1,2-amino alcohols, 5-substituted oxazolidinones, phase-transfer catalysis, carbonylation reaction

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Letters in Organic Chemistry

Title: S,S-Dimethyl Dithiocarbonate as a Valuable Starting Material for the Synthesis of 5-Substituted Oxazolidinones Under Solid-Liquid Phase Transfer Catalysis (SL-PTC) Conditions

Volume: 3 Issue: 11

Author(s): Dario Landini, Matteo Salsa, Gianni Carvoli and Ilir Pecnikaj

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Keywords: S,S-dimethyldithiocarbonate, 1,2-amino alcohols, 5-substituted oxazolidinones, phase-transfer catalysis, carbonylation reaction

Abstract: N-Alkyl and N-aryl 5-substituted oxazolidinones 12-19 were prepared in good to excellent yields by reaction of N-alkyl and N-aryl 1,2-amino alcohols 3-10 with S,S-dimethyldithiocarbonate (11) in the presence of solid NaOH under SL-PTC conditions. The procedure is particularly suitable for scale-up the process involving the use of cheap and ecosafe reagents under mild reaction conditions.

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Landini Dario, Salsa Matteo, Carvoli Gianni and Pecnikaj Ilir, S,S-Dimethyl Dithiocarbonate as a Valuable Starting Material for the Synthesis of 5-Substituted Oxazolidinones Under Solid-Liquid Phase Transfer Catalysis (SL-PTC) Conditions, Letters in Organic Chemistry 2006; 3 (11) . https://dx.doi.org/10.2174/157017806779117111