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

Autor: Maaroof Zarei, Aliasghar Jarrahpour
Jazyk: angličtina
Rok vydání: 2007
Předmět:
Zdroj: Molecules, Vol 12, Iss 10, Pp 2364-2379 (2007)
Druh dokumentu: article
ISSN: 1420-3049
DOI: 10.3390/12102364
Popis: 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.
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