Synlett 2019; 30(20): 2247-2252
DOI: 10.1055/s-0039-1690734
letter
© Georg Thieme Verlag Stuttgart · New York

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

Toshiki Yamashiro
,
Koji Yamada
,
Haruka Yoshida
,
Yutaro Tomisaka
,
Takahide Nishi
,
Takumi Abe
This work was financially supported by a Grant-in-Aid for Young Scientists (B) (Grant No. 16K18849 for T. A.) from the Japan Society for the Promotion of Science (JSPS).
Further Information

Publication History

Received: 25 September 2019

Accepted after revision: 15 October 2019

Publication Date:
05 November 2019 (online)

Abstract

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.

Supporting Information

 
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