Intramolecular Photochemical Cross-Coupling Reactions of 3-Acyl-2-haloindoles and 2-Chloropyrrole-3-carbaldehydes with Substituted Benzenes

Highly efficient syntheses of indolo[2,1‐a]isoquinolines, indolo[2,1‐a][2]benzazepines, pyrrolo[2,1‐a]isoquinolines and pyrrolo[1,2‐a]benzazepines in excellent yields have been achieved by the intramolecular photochemical cross‐coupling reactions of 3‐acyl‐2‐halo‐N‐(ω‐arylalkyl)indoles and 2‐chloro‐...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2009-11, Vol.351 (17), p.2839-2844
Main Authors: Lu, Shen-Ci, Zhang, Xi-Xia, Shi, Zong-Jun, Ren, Yu-Wei, Li, Bing, Zhang, Wei
Format: Article
Language:English
Subjects:
1-a]benzazepines
1-a]isoquinolines
2-chloro-N-(ω-arylalkyl)indole-3-carbaldehydes
2-chloro-N-(ω-arylalkyl)pyrrole-3-carbaldehydes
cross-coupling
indolo
indolo[2,1‐a]benzazepines
indolo[2,1‐a]isoquinolines
photocyclization
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Summary:Highly efficient syntheses of indolo[2,1‐a]isoquinolines, indolo[2,1‐a][2]benzazepines, pyrrolo[2,1‐a]isoquinolines and pyrrolo[1,2‐a]benzazepines in excellent yields have been achieved by the intramolecular photochemical cross‐coupling reactions of 3‐acyl‐2‐halo‐N‐(ω‐arylalkyl)indoles and 2‐chloro‐N‐(ω‐arylalkyl)pyrrole‐3‐carbaldehydes in acetone. A new heterocyclic ring system – pyrrolo[1,2‐d][1,4]benzoxazepine – has also been constructed for the first time in this work by the photocyclization of 2‐chloro‐N‐(2‐phenoxyethyl)pyrrole‐3‐carbaldehyde.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.200900540