Preferential intramolecular ring closure of aminoalcohols with diethyl carbonate to oxazolidinones.
The closure by cyclization with diethyl carbonate (EtO)(2)CO from aminoalcohols 1 as starting material can lead to the oxazolidinones 2a, b and 2c, respectively. In the reaction of trans-isomer (6) and (EtO)(2)CO, isolated products were also only 5-membered oxazolidinone derivative (7), containing its dehydrated derivative 8. The preferential formation of the 5-membered oxazolidinone ring system apparently indicated that this process (5-Exo-Trig ring closure) is more favorable than that of 6- or 7-membered ring derivative (3 or 9) by 6- or 7-Exo-Trig ring closure.
Fujisaki
Fumiko
F
Faculty of Pharmaceutical Science, Fukuoka University, Nanakuma, Fukuoka 814-0180, Japan.
Oishi
Marumi
M
Sumoto
Kunihiro
K
D000605:Amino Alcohols / Q000138:chemical synthesis*; D002855:Chromatography, Thin Layer; D003500:Cyclization; D004047:Diethyl Pyrocarbonate / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D023303:Oxazolidinones / Q000138:chemical synthesis*; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013055:Spectrophotometry, Infrared
D000605:Amino Alcohols; D007202:Indicators and Reagents; D023303:Oxazolidinones; C017858:ethyl carbonate; D004047:Diethyl Pyrocarbonate