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

Molecules

Aliasghar Jarrahpour¹ 

关键词: 2-Azetidinones;    N-insubstituted β-Lactam;    ceric ammonium nitrate;    Staudinger reaction;    p-ethoxyphenyl (PEP) group.;   

DOI  :  10.3390/12102364

来源: mdpi

【 摘 要 】

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)-2-azetidinones 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.

【 授权许可】

Unknown   
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