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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

Author:
Zhu, Wenju, Tong, Shuo, Zhu, Jieping, Wang, Mei-Xiang
Source:
Journal of organic chemistry 2019 v.84 no.5 pp. 2870-2878
ISSN:
1520-6904
Subject:
alkaloids, aromatic hydrocarbons, arylation, chemical structure, cross-coupling reactions, dehydrogenation, heterocyclic nitrogen compounds, organic chemistry
Abstract:
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.
Agid:
6323077