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 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 compound...
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| Format: | Article |
| Language: | English |
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MDPI AG
2007-10-01
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| Series: | Molecules |
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| Online Access: | http://www.mdpi.com/1420-3049/12/10/2364/ |
| _version_ | 1819267279042379776 |
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| author | Maaroof Zarei Aliasghar Jarrahpour |
| author_facet | Maaroof Zarei Aliasghar Jarrahpour |
| author_sort | Maaroof Zarei |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-12-23T21:14:38Z |
| format | Article |
| id | doaj.art-14b0e32025964b0791e26c66ba2c9c1b |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-23T21:14:38Z |
| publishDate | 2007-10-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-14b0e32025964b0791e26c66ba2c9c1b2022-12-21T17:30:57ZengMDPI AGMolecules1420-30492007-10-0112102364237910.3390/12102364Synthesis of Novel N-(4-Ethoxyphenyl) Azetidin-2-ones and Their Oxidative N-Deprotection by Ceric Ammonium NitrateMaaroof ZareiAliasghar JarrahpourIt 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.http://www.mdpi.com/1420-3049/12/10/2364/-AzetidinonesN-insubstituted β-Lactamceric ammonium nitrate2-AzetidinonesN-insubstituted β-Lactamceric ammonium nitrateStaudinger reactionp-ethoxyphenyl (PEP) group |
| spellingShingle | Maaroof Zarei Aliasghar Jarrahpour Synthesis of Novel N-(4-Ethoxyphenyl) Azetidin-2-ones and Their Oxidative N-Deprotection by Ceric Ammonium Nitrate Molecules -Azetidinones N-insubstituted β-Lactam ceric ammonium nitrate 2-Azetidinones N-insubstituted β-Lactam ceric ammonium nitrate Staudinger reaction p-ethoxyphenyl (PEP) group |
| title | Synthesis of Novel N-(4-Ethoxyphenyl) Azetidin-2-ones and Their Oxidative N-Deprotection by Ceric Ammonium Nitrate |
| title_full | Synthesis of Novel N-(4-Ethoxyphenyl) Azetidin-2-ones and Their Oxidative N-Deprotection by Ceric Ammonium Nitrate |
| title_fullStr | Synthesis of Novel N-(4-Ethoxyphenyl) Azetidin-2-ones and Their Oxidative N-Deprotection by Ceric Ammonium Nitrate |
| title_full_unstemmed | Synthesis of Novel N-(4-Ethoxyphenyl) Azetidin-2-ones and Their Oxidative N-Deprotection by Ceric Ammonium Nitrate |
| title_short | Synthesis of Novel N-(4-Ethoxyphenyl) Azetidin-2-ones and Their Oxidative N-Deprotection by Ceric Ammonium Nitrate |
| title_sort | synthesis of novel n 4 ethoxyphenyl azetidin 2 ones and their oxidative n deprotection by ceric ammonium nitrate |
| topic | -Azetidinones N-insubstituted β-Lactam ceric ammonium nitrate 2-Azetidinones N-insubstituted β-Lactam ceric ammonium nitrate Staudinger reaction p-ethoxyphenyl (PEP) group |
| url | http://www.mdpi.com/1420-3049/12/10/2364/ |
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