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Intramolecular Arylation of Tertiary Enamides through Pd(OAc)₂-Catalyzed Dehydrogenative Cross-Coupling Reaction: Construction of Fused N-Heterocyclic Scaffolds and Synthesis of Isoindolobenzazepine Alkaloids
- Zhu, Wenju, Tong, Shuo, Zhu, Jieping, Wang, Mei-Xiang
- Journal of organic chemistry 2019 v.84 no.5 pp. 2870-2878
- alkaloids, aromatic hydrocarbons, arylation, chemical structure, cross-coupling reactions, dehydrogenation, heterocyclic nitrogen compounds, organic chemistry
- Pd(OAc)₂-catalyzed intramolecular dehydrogenative cross-coupling reaction between tertiary enamides, which were derived from the condensation of 2-arylethylamines and methyl o-acetylbenzoate, and arenes enabled synthesis of 7,8-dihydro-5H-benzo[4,5]azepino[2,1-a]isoindol-5-one derivatives under mild conditions. The synthetic method was applied in the total synthesis of aporhoeadane alkaloids palmanine, lennoxamine, and chilenamine in only three or four steps.