Synthesis of novel N-(4-ethoxyphenyl) azetidin-2-ones and their oxidative N-deprotection by ceric ammonium nitrate.
It is shown that the N-(p-ethoxyphenyl) group on beta-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.
Jarrahpour
Aliasghar
A
Department of Chemistry, College of Sciences, Shiraz University, Shiraz 71454, Iran. jarrah@chem.susc.ac.ir
Zarei
Maaroof
M
D001384:Azetidines / Q000138:chemical synthesis* / Q000737:chemistry*; D002563:Cerium / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D012997:Solvents / Q000737:chemistry; D013696:Temperature; D047090:beta-Lactams / Q000737:chemistry
C116379:2-azetidinone; D001384:Azetidines; D012997:Solvents; D047090:beta-Lactams; D002563:Cerium; C004653:ceric ammonium nitrate