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Synthesis of Cyclopenta[b]indol-1-ones and Carbazol-4-ones from N-(2-Halophenyl)-Substituted Enaminones by Intramolecular Heck Reaction

✍ Scribed by Ulrik S. Sørensen; Esteban Pombo-Villar

Publisher: John Wiley and Sons
Year: 2004
Tongue: German
Weight: 119 KB
Volume: 87
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.200490020

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✦ Synopsis

Abstract

An efficient synthetic route towards N‐methylated or nonmethylated 3,4‐dihydrocyclopent[b]indol‐1(2__H__)‐ones (3) and 1,2,3,9‐tetrahydrocarbazol‐4(4__H__)‐one (10) was elaborated, based on Pd‐catalyzed intramolecular Heck reaction. The chemoselectivity of the cyclization was studied in the case of the bi‐ and trifunctional substrates 12 and 17, respectively. In the latter case, depending on the catalyst, either the brominated indole 18 or the tetracyclic compound 19 were obtained by single and double Heck reaction, respectively.

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