Ruthenium(II)-Catalyzed Migratory C–H Allylation/Hydroamination Cascade for the Synthesis of Rutaecarpine Analogues
| Autor: | Gurupada Bairy, Arijit Nandi, Ranjan Jana, Kartic Manna |
|---|---|
| Rok vydání: | 2019 |
| Předmět: |
Annulation
010405 organic chemistry Organic Chemistry chemistry.chemical_element Rutaecarpine 010402 general chemistry 01 natural sciences Medicinal chemistry Catalysis 0104 chemical sciences Ruthenium chemistry.chemical_compound chemistry Cascade reaction Quinazoline Moiety Hydroamination Quinazolinone |
| Zdroj: | Synthesis. 51:2523-2531 |
| ISSN: | 1437-210X 0039-7881 |
| DOI: | 10.1055/s-0037-1611525 |
| Popis: | An unprecedented allyl migration from a remote position of a quinazoline moiety through a ruthenium(II) shuttle is reported. This present cascade reaction is initiated through the formation of an η3-ruthenium–allyl complex followed by C–H allylation at the ortho position of the 2-aryl moiety. Finally, hydroamination with the quinazolinone -NH group, which is formed through tautomerization of the quinazoline, furnishes the annulation product. This exceedingly fast cascade reaction is complete within 10 minutes to provide rutaecarpine analogues in a single operation. |
| Databáze: | OpenAIRE |
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