Revisiting 2-Alkoxy-3-bromoindolines: Control C-2 vs. C-3 elimination for Regioselective synthesis of alkoxyindoles

Takumi Abe, Yuta Kosaka, Takaaki Kawasaki, Yuki Ohata, Toshiki Yamashiro, Koji Yamada

Research output: Contribution to journalArticlepeer-review

2 Citations (Scopus)

Abstract

The regioselective synthesis of both 2-and 3-Alkoxyindoles from a common intermediate, 2-Alkoxy-3-bromoindolines (ROBIN), is described. The 2-Alkoxyindoles are obtained by a base-promoted regioselective elimination of HBr from ROBIN, whereas the synthesis of 3-Alkoxyindoles is achieved by a silvermediated alkoxylation followed by an acid-promoted elimination of alkoxide. This key elimination features the complete regioselectivity and no need for catalysts, that makes it have potential synthetic applications. Furthermore, this protocol is user friendly because ROBIN is able to be prepared from commercially available indoles and is a bench-stable easy-To-handle crystalline substrate, thus allowing the concise synthesis of a variety of both 2-and 3-Alkoxyindoles.

Original languageEnglish
Pages (from-to)555-558
Number of pages4
JournalChemical and Pharmaceutical Bulletin
Volume68
Issue number6
DOIs
Publication statusPublished - 2020
Externally publishedYes

Keywords

  • 2-Alkoxyindole
  • 3-Alkoxyindole
  • elimination
  • regioselective synthesis
  • silver

ASJC Scopus subject areas

  • Chemistry(all)
  • Drug Discovery

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