Preferential intramolecular ring closure of aminoalcohols with diethyl carbonate to oxazolidinones

Chem Pharm Bull (Tokyo). 2007 May;55(5):829-31. doi: 10.1248/cpb.55.829.

Abstract

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.

MeSH terms

  • Amino Alcohols / chemical synthesis*
  • Chromatography, Thin Layer
  • Cyclization
  • Diethyl Pyrocarbonate / analogs & derivatives*
  • Diethyl Pyrocarbonate / chemical synthesis
  • Indicators and Reagents
  • Magnetic Resonance Spectroscopy
  • Oxazolidinones / chemical synthesis*
  • Spectrometry, Mass, Fast Atom Bombardment
  • Spectrophotometry, Infrared

Substances

  • Amino Alcohols
  • Indicators and Reagents
  • Oxazolidinones
  • ethyl carbonate
  • Diethyl Pyrocarbonate