Transition-Metal-Free Quinoline Synthesis from Acetophenones and Anthranils via Sequential One-Carbon Homologation/Conjugate Addition/Annulation Cascade

A transition-metal-free method for the construction of functionalized quinolines from readily available acetophenones and anthranils is reported. This one-pot reaction cascade involves in situ generation of α,β-unsaturated ketones from the acetophenone via one-carbon homologation by DMSO followed by...

Full description

Saved in:
Bibliographic Details
Published in:Organic letters 2017-09, Vol.19 (18), p.4948-4951
Main Authors: Wakade, Sandip Balasaheb, Tiwari, Dipak Kumar, Ganesh, Pothapragada S. K. Prabhakar, Phanindrudu, Mandalaparthi, Likhar, Pravin R, Tiwari, Dharmendra Kumar
Format: Article
Language:English
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:A transition-metal-free method for the construction of functionalized quinolines from readily available acetophenones and anthranils is reported. This one-pot reaction cascade involves in situ generation of α,β-unsaturated ketones from the acetophenone via one-carbon homologation by DMSO followed by the aza-Michael addition of anthranils and subsequent annulation. DMSO acted in this reaction not only as solvent but also as one carbon source, thus providing a highly atom-economical and environmentally benign approach for the synthesis of 3-substituted quinolines.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.7b02429