| Autor: |
Holt JJ; Department of Chemistry, The State University of New York at Buffalo, Buffalo, New York 14260-3000, USA., Calitree BD, Vincek J, Gannon MK 2nd, Detty MR |
| Jazyk: |
angličtina |
| Zdroj: |
The Journal of organic chemistry [J Org Chem] 2007 Mar 30; Vol. 72 (7), pp. 2690-3. Date of Electronic Publication: 2007 Mar 03. |
| DOI: |
10.1021/jo070086f |
| Abstrakt: |
9-formyljulolidine was oxidized via a microwave-assisted Willgerodt-Kindler reaction to the N-piperidine or N-morpholine julolidine-9-thioamide. 9-formyl-1,1,7,7-tetramethyljulolidine gave the corresponding N-piperidine tetramethyljulolidine-9-thioamide. The thioamides were converted to the corresponding carboxamides with trifluoroacetic anhydride. The amide group directed ortho-metalation in the julolidine system, but not in the tetramethyljulolidine system. The resulting anion was captured by dichalcogenide electrophiles. The resulting products were converted to chalcogenoxanthones with phosphorus oxychloride and triethylamine (POCl3/Et3N). |
| Databáze: |
MEDLINE |
| Externí odkaz: |
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