Expeditious synthesis of multisubstituted indoles via multiple hydrogen transfers.

Expeditious synthesis of multisubstituted indoles via multiple hydrogen transfers.
Chem Commun (Camb). 2018 Oct 09;:
Authors: Yoshida T, Mori K
Abstract
Described herein is the expeditious construction of multi-substituted indole skeletons via multiple hydrogen transfers. When ortho-amino ketoesters were treated with a catalytic amount of TiCl4 in the presence of 1.0 equivalent of dehydrating reagent, three types of hydrogen transfer processes ([1,5]-hydride shift, proton transfer, and [1,2]-hydride shift) occurred to give various 3-alkoxycarbonylindoles. Further study revealed that a [1,2]-alkyl shift instead of a [1,2]-hydride shift proceeded to afford 3-alkylindoles from the substrates with an amino group having tertiary carbons adjacent to a nitrogen atom.
PMID: 30298159 [PubMed - as supplied by publisher]

Source: Chemical Communications - October 9, 2018 Category: Chemistry Authors: Yoshida T, Mori K Tags: Chem Commun (Camb) Source Type: research