Enantioselective N‑Heterocyclic Carbene-Catalyzed Synthesis of Spirocyclic Oxindole-benzofuroazepinones
journal contributionposted on 23.11.2018, 00:00 by Zhong-Hua Gao, Kun-Quan Chen, Yan Zhang, Ling-Mei Kong, Yan Li, Song Ye
Herein, we report an enantioselective synthesis of azepinones via the N-heterocyclic carbene (NHC) catalyzed [3+4] annulation reaction of isatin-derived enals and aurone-derived azadienes. The corresponding spirocyclic oxindole-benzofuroazepinones were obtained in good yields, with excellent diastereo- and enantioselectivities. The resulted azepinones were evaluated for their in vitro cytotoxic activities against six human tumor cell lines, with two compounds showing significant inhibitory activity comparable with that of cisplatin.
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Enantioselectivecisplatincytotoxic activitiesCarbene-Catalyzedtumor cell linesNHCspirocyclic oxindole-benzofuroazepinonesannulationenantioselective synthesisheterocyclic carbeneSpirocyclic Oxindole-benzofuroazepinones Hereinenantioselectivitiecompoundaurone-derived azadienesdiastereoyieldisatin-derived enalsSynthesi