Solid-phase synthesis of oxazolidinones by cycloaddition of resin-bound epoxides with isocyanates.
The first solid-phase synthesis of oxazolidinones by cycloaddition of resin-bound epoxides with isocyanates is described. Synthesis of the title compounds was achieved by alkylation of resin-bound carbamates with glycidyl tosylate, followed by cycloaddition of the resulting epoxides with isocyanates at elevated temperature in high yields and purity. Because N-aryloxazolidinones have been known to possess various biological activities, this method is useful from the viewpoint of drug discovery.
Buchstaller
Hans-Peter
HP
Merck KGaA, Medicinal Chemistry Research Laboratories, Frankfurter Strasse 250, D-64271 Darmstadt, Germany.
D004852:Epoxy Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D017953:Isocyanates / Q000138:chemical synthesis* / Q000737:chemistry; D023303:Oxazolidinones / Q000138:chemical synthesis* / Q000737:chemistry; D013678:Technology, Pharmaceutical / Q000379:methods*
D004852:Epoxy Compounds; D017953:Isocyanates; D023303:Oxazolidinones