Zinc (II)-Mediated Selective O-Benzylation of 2-Oxo-1,2-Dihydropyridines Systems
The selective O-benzylation of 2-oxo-1,2-dihydropyridines plays a critical role in organic synthesis of natural products and biological active molecules. Herein we report a novel ternary system of ZnO, ZnCl2 and N,N-diisopropylethylamine (DIEA), that is highly effective for selective O-benzylation o...
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MDPI AG
2018-07-01
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| Series: | Molecules |
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| Online Access: | http://www.mdpi.com/1420-3049/23/7/1784 |
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| author | Qifan Zhou Fangyu Du Xinjie Liang Wenqiang Liu Ting Fang Guoliang Chen |
| author_facet | Qifan Zhou Fangyu Du Xinjie Liang Wenqiang Liu Ting Fang Guoliang Chen |
| author_sort | Qifan Zhou |
| collection | DOAJ |
| description | The selective O-benzylation of 2-oxo-1,2-dihydropyridines plays a critical role in organic synthesis of natural products and biological active molecules. Herein we report a novel ternary system of ZnO, ZnCl2 and N,N-diisopropylethylamine (DIEA), that is highly effective for selective O-benzylation of 2-oxo-1,2-dihydropyridines using abundant substituted benzyl halides and related substituted 2-oxo-1,2-dihydropyridines compounds. This process allows access to a variety of O-benzyl products under mild reaction conditions, which are important synthetic intermediates in the protection of functional groups, and represents a new method toward the development for the O-benzylation of 2-oxo-1,2-dihydropyridines. |
| first_indexed | 2024-12-23T04:51:27Z |
| format | Article |
| id | doaj.art-2bcd7b1ab5844989b2737d0a0ccbed5e |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-23T04:51:27Z |
| publishDate | 2018-07-01 |
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| spelling | doaj.art-2bcd7b1ab5844989b2737d0a0ccbed5e2022-12-21T17:59:26ZengMDPI AGMolecules1420-30492018-07-01237178410.3390/molecules23071784molecules23071784Zinc (II)-Mediated Selective O-Benzylation of 2-Oxo-1,2-Dihydropyridines SystemsQifan Zhou0Fangyu Du1Xinjie Liang2Wenqiang Liu3Ting Fang4Guoliang Chen5Key Laboratory of Structure-Based Drug Design & Discovery of Ministry of Education, Shenyang Pharmaceutical University, Shenyang 110016, ChinaKey Laboratory of Structure-Based Drug Design & Discovery of Ministry of Education, Shenyang Pharmaceutical University, Shenyang 110016, ChinaKey Laboratory of Structure-Based Drug Design & Discovery of Ministry of Education, Shenyang Pharmaceutical University, Shenyang 110016, ChinaKey Laboratory of Structure-Based Drug Design & Discovery of Ministry of Education, Shenyang Pharmaceutical University, Shenyang 110016, ChinaKey Laboratory of Structure-Based Drug Design & Discovery of Ministry of Education, Shenyang Pharmaceutical University, Shenyang 110016, ChinaKey Laboratory of Structure-Based Drug Design & Discovery of Ministry of Education, Shenyang Pharmaceutical University, Shenyang 110016, ChinaThe selective O-benzylation of 2-oxo-1,2-dihydropyridines plays a critical role in organic synthesis of natural products and biological active molecules. Herein we report a novel ternary system of ZnO, ZnCl2 and N,N-diisopropylethylamine (DIEA), that is highly effective for selective O-benzylation of 2-oxo-1,2-dihydropyridines using abundant substituted benzyl halides and related substituted 2-oxo-1,2-dihydropyridines compounds. This process allows access to a variety of O-benzyl products under mild reaction conditions, which are important synthetic intermediates in the protection of functional groups, and represents a new method toward the development for the O-benzylation of 2-oxo-1,2-dihydropyridines.http://www.mdpi.com/1420-3049/23/7/1784O-benzylationN-benzylation2-oxo-1,2-dihydropyridineszinc (II)selectivity |
| spellingShingle | Qifan Zhou Fangyu Du Xinjie Liang Wenqiang Liu Ting Fang Guoliang Chen Zinc (II)-Mediated Selective O-Benzylation of 2-Oxo-1,2-Dihydropyridines Systems Molecules O-benzylation N-benzylation 2-oxo-1,2-dihydropyridines zinc (II) selectivity |
| title | Zinc (II)-Mediated Selective O-Benzylation of 2-Oxo-1,2-Dihydropyridines Systems |
| title_full | Zinc (II)-Mediated Selective O-Benzylation of 2-Oxo-1,2-Dihydropyridines Systems |
| title_fullStr | Zinc (II)-Mediated Selective O-Benzylation of 2-Oxo-1,2-Dihydropyridines Systems |
| title_full_unstemmed | Zinc (II)-Mediated Selective O-Benzylation of 2-Oxo-1,2-Dihydropyridines Systems |
| title_short | Zinc (II)-Mediated Selective O-Benzylation of 2-Oxo-1,2-Dihydropyridines Systems |
| title_sort | zinc ii mediated selective o benzylation of 2 oxo 1 2 dihydropyridines systems |
| topic | O-benzylation N-benzylation 2-oxo-1,2-dihydropyridines zinc (II) selectivity |
| url | http://www.mdpi.com/1420-3049/23/7/1784 |
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