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Synthesis of β-, γ-, and δ-Lactams via Pd(II)-Catalyzed C-H Activation
| Content Provider | Scilit |
|---|---|
| Author | Wasa, M. |
| Editor | Yu, J. -Q. |
| Copyright Year | 2008 |
| Description | Reported is the Pd(II)-catalyzed synthesis of β-, γ-, and δ-lactams via an intramolecular C-H amination strategy. Cyclization of O-methylhydroxamic acids 1 proceeds smoothly under the reaction conditions to deliver γ- and δ-lactams 2 in excellent yields. Although the electronic nature of the arene has little effect on the reaction, the presence of ortho-hydrogens $(R^{²},R^{³}$ = H) greatly retards the reaction. The α,β-double bond in 3 is tolerated, allowing access to oxindoles 4 suitable for further functionalization. The reaction was also extended to the synthesis of 2-quinolone derivatives 6. Attempted formation of a β-lactam under the standard conditions led instead to a β-chlorination product, which was converted into the corresponding lactam on treatment with CsF. Cleavage of the N-methoxy protecting group was readily achieved by hydrogenolysis. |
| Related Links | http://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-0028-1087465.pdf |
| Ending Page | 0023 |
| Page Count | 1 |
| Starting Page | 0023 |
| ISSN | 18611958 |
| e-ISSN | 1861194X |
| DOI | 10.1055/s-0028-1087465 |
| 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 Functionalization |
| Content Type | Text |
| Resource Type | Article |
