In(OTf)-catalysed easy access to dihydropyranocoumarin and dihydropyranochromone derivatives

We developed an easy, In(OTf) 3 -catalysed, regioselective and generalizable method, for allylation/cyclization of β-ketolactone-type heterocyclic compounds. This reaction is proposed to proceed one-pot, through a Friedel-Crafts C -allylation followed by cyclization. This process represents a green...

Full description

Saved in:
Bibliographic Details
Published in:New journal of chemistry 2020-04, Vol.44 (15), p.642-652
Main Authors: Boufroua, Naouel, Dunach, Elisabet, Fontaine-Vive, Fabien, Achouche-Bouzroura, Samia, Poulain-Martini, Sophie
Format: Article
Language:English
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:We developed an easy, In(OTf) 3 -catalysed, regioselective and generalizable method, for allylation/cyclization of β-ketolactone-type heterocyclic compounds. This reaction is proposed to proceed one-pot, through a Friedel-Crafts C -allylation followed by cyclization. This process represents a green synthetic method, as AcOH is the only isolated byproduct. We propose here, a protocol applicable for the construction of biologically active dihydropyranocoumarin and dihydropyranochromone derivatives. Allylation/cyclization of β-ketolactone-type heterocyclic compounds, under In(OTf) 3 -catalysis, for the construction of biologically active dihydropyranocoumarin and dihydropyranochromone derivatives.
ISSN:1144-0546
1369-9261
DOI:10.1039/d0nj00080a