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Intramolecular Photochemical Cross‐Coupling Reactions of 3‐Acyl‐2‐haloindoles and 2‐Chloropyrrole‐3‐carbaldehydes with Substituted Benzenes
Author(s) -
Lu ShenCi,
Zhang XiXia,
Shi ZongJun,
Ren YuWei,
Li Bing,
Zhang Wei
Publication year - 2009
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200900540
Subject(s) - chemistry , intramolecular force , benzazepines , pyrrole , ring (chemistry) , acetone , annulation , medicinal chemistry , photochemistry , stereochemistry , organic chemistry , catalysis
Abstract 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.