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Synthesis of 2-Substituted Pyridine N-Oxides via Directed ortho-Metalation
| Content Provider | Scilit |
|---|---|
| Author | Andersson, H. Gustafsson, M. Olsson, R. Almqvist, F. |
| Copyright Year | 2008 |
| Description | Reported is the directed ortho-metalation of pyridine N-oxides using i-PrMgCl to give 2-substituted Grignard species which may be trapped with electrophiles to give the corresponding 2-substituted pyridine N-oxides in low to excellent yields. The method appears to be an improvement on the use of alkyllithium reagents at -78 ˚C which is known to produce mainly 2,6-disubstituted products in low to moderate yields (14-45%) (R. A. Abramovitch et al. J. Org. Chem. 1972, 37, 1690; see Review below). In the case of 3,5-dimethylpyridine N-oxide, the 2-magnesiated species was subjected to interesting cross-coupling conditions using a diphenyliodonium partner to give a 2-phenyl product in a moderate yield of 51%. Review: M. Schlosser, F. Mongin Chem. Soc. Rev. 2007, 36, 1161-1172. |
| Related Links | http://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-0028-1087462.pdf |
| Ending Page | 0025 |
| Page Count | 1 |
| Starting Page | 0025 |
| ISSN | 18611958 |
| e-ISSN | 1861194X |
| DOI | 10.1055/s-0028-1087462 |
| Journal | Synfacts |
| Issue Number | 01 |
| Volume Number | 2009 |
| Language | English |
| Publisher | Georg Thieme Verlag KG |
| Publisher Date | 2008-12-18 |
| Access Restriction | Open |
| Subject Keyword | Journal: Synfacts Organic Chemistry Em Class |
| Content Type | Text |
| Resource Type | Article |
