A competitive and highly selective 7-, 6- and 5-annulation with 1,3-migration through C-H and N-H - alkyne coupling
| Autor: | Dilip K. Maiti, Sk Ajarul, Tanmay K. Pati, Anirban Kayet |
|---|---|
| Rok vydání: | 2019 |
| Předmět: |
chemistry.chemical_classification
Annulation Chemistry Metals and Alloys Alkyne General Chemistry Highly selective Medicinal chemistry Catalysis Surfaces Coatings and Films Electronic Optical and Magnetic Materials Coupling (electronics) Yield (chemistry) Materials Chemistry Ceramics and Composites Surface modification |
| Zdroj: | Chemical communications (Cambridge, England). 56(3) |
| ISSN: | 1364-548X |
| Popis: | We demonstrated a highly competitive and selective C–C and N–C cross-coupled 7-, 6- and 5-annulation utilizing 2-ethynylanilides to afford functionalized 1H-benzo[b]azepin-2(5H)-ones, 2-quinolinones, and 3-acylindoles in high yield. ZnCl2 was found to be the smart catalyst for 7- and 5-annulation with 1,3-migration through C–H and N–H functionalization, respectively, whereas molecular iodine performed the C–H functionalized 6-annulation with a nonconventional 1,3 H-shift. The mechanism was investigated by intermediate trapping, control, and labeling experiments. |
| Databáze: | OpenAIRE |
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