Synthesis of Novel N-(4-Ethoxyphenyl) Azetidin-2-ones and Their Oxidative N-Deprotection by Ceric Ammonium Nitrate

Aliasghar Jarrahpour, Maaroof Zarei
2007 Molecules  
It is shown that the N-(p-ethoxyphenyl) group on β-lactams can be oxidatively removed by ceric ammonium nitrate in good yield. Fourteen new N-(p-ethoxyphenyl)-2azetidinones 8a-n were synthesized through standard [2+2] ketene-imine cycloadditions (Staudinger reaction). Treatment of these compounds with ceric ammonium nitrate yielded the N-dearylated 2-azetidinones 9a-n in good to excellent yields. The effects of solvent, molar equiv of CAN and different temperatures have been investigated and optimum conditions were established.
doi:10.3390/12102364 pmid:17978763 fatcat:gsjhhueo2nhqfevgb7asfdnb2u