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Regioselective Synthesis of Indole-Fused Seven-Membered N-Heterocycles via Photoredox-Catalyzed Intramolecular Cyclization. 2022

Ziqin Zhang, and Yifeng Chen, and Linrong He, and Lihua Xie, and Zhitao Chen
School of Pharmacy, Fujian Medical University, Fuzhou 350122, China.

Herein, we describe the construction of indole-fused seven-membered N- and O-heterocycles from indolyl α-diazocarbonyls via photoredox-catalyzed intramolecular cyclization. The photoredox process features operational simplicity, mild conditions, and as low as 0.1 mol % catalyst loading. The tricyclic heterocycles are obtained in yields of 24 to 67% with excellent regioselectivity. The practicality of this protocol is further demonstrated by gram-scale reactions carried out in both batch and continuous flow.

UI MeSH Term Description Entries
D007211 Indoles Benzopyrroles with the nitrogen at the number one carbon adjacent to the benzyl portion, in contrast to ISOINDOLES which have the nitrogen away from the six-membered ring.
D002384 Catalysis The facilitation of a chemical reaction by material (catalyst) that is not consumed by the reaction. Catalyses
D003500 Cyclization Changing an open-chain hydrocarbon to a closed ring. (McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed) Cyclizations

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