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Synthesis of Polysubstituted Pyrroles via Dihydro-1,2-oxazines
| Content Provider | Scilit |
|---|---|
| Copyright Year | 2006 |
| Description | A method for the synthesis of polysubstituted pyrroles via Diels-Alder adducts derived from the reaction of dienes with tert-butyl N-hydroxycarbamate is reported. The reaction of the dienes with tert-butyl N-oxocarbamate, derived by in situ oxidation from N-Boc-hydroxylÂamine leads to oxazines in good to excellent yields and regioselectivities from 55:45 to 2:98 depending on the diene. Reductive ring opening using $NaBH_{4}$ in the presence of $Mo(CO)_{6}$ gave the corresponding amino alcohols which, under $MnO_{2}$ or Dess-Martin periodinane oxidative conditions and subsequent cyclization, led to the final pyrrole derivatives in excellent yields. |
| Related Links | http://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-2006-931969.pdf |
| Ending Page | 0204 |
| Page Count | 1 |
| Starting Page | 0204 |
| ISSN | 18611958 |
| e-ISSN | 1861194X |
| DOI | 10.1055/s-2006-931969 |
| Journal | Synfacts |
| Issue Number | 03 |
| Volume Number | 2006 |
| Language | English |
| Publisher | Georg Thieme Verlag KG |
| Publisher Date | 2006-02-21 |
| Access Restriction | Open |
| Subject Keyword | Journal: Synfacts Organic Chemistry Excellent Yields Polysubstituted Pyrroles |
| Content Type | Text |
| Resource Type | Article |