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Polarized Ketene Dithioacetals; 53:1A Facile Synthesis of 2-Aryl-6-methylthio-4H-pyran-4-ones and a Novel Cycloaromatization Reaction
| Content Provider | Scilit |
|---|---|
| Author | Ila, H. Junjappa, H. |
| Editor | Singh, L. W. |
| Copyright Year | 1987 |
| Description | A facile route to hitherto unreported 2-aryl-6-methylthio-4H-pyran-4-ones 4a-f has been developed by base-catalyzed condensation of acylketene dithioacetal 2 with substituted methyl benzoates 1a-f followed by subsequent ring closure of resulting α-aroylacylketene dithioacetals 3a-f. Acylketene dithioacetal 2 and the corresponding β-methylthioenone 9 are shown to undergo self-condensation and aromatization in the presence of sodium hydride and methylbenzoate in refluxing xylene to give 2, 6-bis(methylthio)-4-hydroxy-acetophenone (6) and 4-hydroxyacetophenone (10) respectively in good yields. A mechanistic pathway for the formation of 6 and 10 via 3 has been described. |
| Related Links | http://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-1987-28107.pdf |
| Ending Page | 875 |
| Page Count | 3 |
| Starting Page | 873 |
| ISSN | 00397881 |
| e-ISSN | 1437210X |
| DOI | 10.1055/s-1987-28107 |
| Journal | Synthesis |
| Issue Number | 10 |
| Volume Number | 1987 |
| Language | English |
| Publisher | Georg Thieme Verlag KG |
| Publisher Date | 1987-01-01 |
| Access Restriction | Open |
| Subject Keyword | Journal: Synthesis Organic Chemistry |
| Content Type | Text |
| Resource Type | Article |
| Subject | Organic Chemistry Catalysis |
