4.4 Article

Silver-Mediated Intramolecular Friedel-Crafts-Type Cyclizations of 2-Benzyloxy-3-bromoindolines: Synthesis of Isochromeno[3,4-b] indolines and 3-Arylindoles

Journal

SYNLETT
Volume 30, Issue 20, Pages 2247-2252

Publisher

GEORG THIEME VERLAG KG
DOI: 10.1055/s-0039-1690734

Keywords

Friedel-Crafts; cyclization; isochromeno[3,4,b]indolines; deformylative arylation; 3-arylindoles; silver

Funding

  1. Japan Society for the Promotion of Science (JSPS) [16K18849]

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We disclose a silver-mediated intramolecular Friedel-Crafts-type cyclization of 2-benzyloxy-3-bromoindolines to afford an untapped family of isochromeno[3,4- b ]indolines and 3-arylindoles, in which deformylative arylation of 2-(4-methoxybenzyloxy)-3-bromoindolines is reported for the first time. The isochromeno[3,4- b ]indolines can be readily transformed into other heterocyclic moieties.

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