炭酸塩を用いるオキサゾリジノン環の新規合成法と反応機構の解明

抄録

Oxazolidinones are the important precursors of amino alcohols and amino acids. We found a simple and convenient synthetic method of oxazolidinones. The reaction of primary amines and halomethyloxiranes with carbonates, such as K₂CO₃, in the presence of base (TEA, DBU) gave oxazolidinones in a high yield. When CO₂ was used instead of carbonates, oxazinones were first obtained predominantly and then converted to oxazolidinones. This conversion to oxazolidinones was confirmed by the use of oxazinones as starting materials in the presence of primary amines, halomethyloxiranes and K₂CO₃. Therefore, we confirmed that oxazinones formed in the reaction process were converted to oxazolidinones. The reaction conditions to improve yields and the use of various amines (e.g. Naltrexamine) were examined.

Scheme 1