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Molecules 2007, 12(10), 2364-2379; doi:10.3390/12102364
Article

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

*  and
Department of Chemistry, College of Sciences, Shiraz University, Shiraz 71454, Iran
* Author to whom correspondence should be addressed.
Received: 20 June 2007 / Revised: 26 August 2007 / Accepted: 26 August 2007 / Published: 25 October 2007
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Abstract

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.
Keywords: -Azetidinones; N-insubstituted β-Lactam; ceric ammonium nitrate; 2-Azetidinones; N-insubstituted β-Lactam; ceric ammonium nitrate; Staudinger reaction; p-ethoxyphenyl (PEP) group -Azetidinones; N-insubstituted β-Lactam; ceric ammonium nitrate; 2-Azetidinones; N-insubstituted β-Lactam; ceric ammonium nitrate; Staudinger reaction; p-ethoxyphenyl (PEP) group
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
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Jarrahpour, A.; Zarei, M. Synthesis of Novel N-(4-Ethoxyphenyl) Azetidin-2-ones and Their Oxidative N-Deprotection by Ceric Ammonium Nitrate. Molecules 2007, 12, 2364-2379.

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