205-45-8Relevant academic research and scientific papers
Mapping the reactivity of the quinoline ring-system – Synthesis of the tetracyclic ring-system of isocryptolepine and regioisomers
H?heim, Katja S.,Urdal Helgeland, Ida T.,Lindb?ck, Emil,Sydnes, Magne O.
, p. 2949 - 2957 (2019/04/25)
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.
