Mapping the reactivity of the quinoline ring-system – Synthesis of the tetracyclic ring-system of isocryptolepine and regioisomers
| Autor: | Katja S. Håheim, Ida T. Urdal Helgeland, Magne O. Sydnes, Emil Lindbäck |
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| Rok vydání: | 2019 |
| Předmět: |
010405 organic chemistry
Chemistry Hydrochloride Organic Chemistry Quinoline chemistry.chemical_element Isocryptolepine 010402 general chemistry Ring (chemistry) 01 natural sciences Biochemistry Medicinal chemistry 0104 chemical sciences Catalysis chemistry.chemical_compound Drug Discovery Structural isomer Reactivity (chemistry) Palladium |
| Zdroj: | Tetrahedron. 75:2949-2957 |
| ISSN: | 0040-4020 |
| DOI: | 10.1016/j.tet.2019.04.026 |
| Popis: | Bromoquinolines (2-bromoquinoline – 8-bromoquinoline and 5-bromo-3-methoxyquinoline) and 2-aminophenylboronic acid hydrochloride were subjected to Suzuki-Miyaura cross-coupling conditions resulting in formation of the desired biaryl systems in good yields. The resulting biaryls were then subjected to palladium catalyzed C H activation/C N bond formation utilizing PdCl2(dppf). The reactions revealed large differences in reactivity depending on the attachment point for the 2-aminophenyl group on the quinoline. The variation in the reactivity was rationalized based on the electron distribution around the quinoline ring-system. |
| Databáze: | OpenAIRE |
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