Convenient synthesis of oxazolidinones by the use of halomethyloxirane, primary amine, and carbonate salt.
[reaction: see text] Primary amines reacted with carbonate salts (Na2CO3, K2CO3, Cs2CO3, and Ag2CO3) and halomethyloxiranes in the presence of a base such as DBU or TEA to give oxazolidinones in high yields. The use of K2CO3 among these carbonate gave the best yield in this synthesis. A reaction mechanism was proposed that the oxazolidinone was obtained from an oxazinanone intermediate via a bicyclo[2.2.1] intermediate. The present reaction can be widely applied to convenient synthesis of useful N-substituted oxazolidinones and chiral oxazolidinones.
Osa
Yumiko
Y
School of Pharmaceutical Sciences, Kitasato University, 5-9-1, Shirokane, Minato-ku, Tokyo 108-8641, Japan.
Hikima
Yuka
Y
Sato
Yoko
Y
Takino
Kouichi
K
Ida
Yoshihiro
Y
Hirono
Shuichi
S
Nagase
Hiroshi
H