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Decarboxylative Cyclization of Ethynyl Benzoxazinanones with Imidazolidines to Access 2,3-Indole-Fused 1,4-Diazocines

Zhangru Cheng, Jiadong Chen, Yulu Zhang, Ying Shao, Jiangtao Sun, Shengbiao Tang

2024Organic Letters13 citationsDOI

Abstract

2,3-Indole-fused 1,4-diazocines represent a new family of indole alkaloid compounds and are difficult to access by the reported protocols. Herein, we report a copper-catalyzed decarboxylative cyclization of cyclic propargylic carbamates with imidazolidines via sequential C-N/C-N/C-C bond formation to deliver a series of 2,3-indole-fused 1,4-diazocines, with a broad substrate scope and mild conditions.

Topics & Concepts

Indole testChemistryStereochemistryIndole alkaloidCombinatorial chemistrySubstrate (aquarium)GeologyOceanographyCatalytic C–H Functionalization MethodsCatalytic Alkyne ReactionsSynthesis of Indole Derivatives
Decarboxylative Cyclization of Ethynyl Benzoxazinanones with Imidazolidines to Access 2,3-Indole-Fused 1,4-Diazocines | Litcius