Issue 19, 2022

The seven-step, one-pot regioselective synthesis of biologically important 3-aryllawsones: scope and applications

Abstract

3-Aryllawsones are well known for their wide range of applications in medicinal chemistry, but their synthesis has always remained challenging as no comprehensive protocol has been outlined to date. Owing to their structural importance, we synthesized various 3-aryllawsones with high regioselectivity from simple lawsone and aldehydes in a seven-step double-cascade one-pot reaction through the combination of organocatalytic Ramachary reductive coupling and Hooker oxidation reactions. The commercial availability of the starting materials, diverse substrate scope, possibility of a one- or two-pot approach, regioselectivity of alkyl transfer (with mechanistic proof provided via X-ray crystal structure analysis), and numerous medicinal applications of 3-aryllawsones are the key attractions of this work.

Graphical abstract: The seven-step, one-pot regioselective synthesis of biologically important 3-aryllawsones: scope and applications

Supplementary files

Article information

Article type
Paper
Submitted
03 Mar 2022
Accepted
17 Mar 2022
First published
18 Mar 2022

Org. Biomol. Chem., 2022,20, 3948-3954

The seven-step, one-pot regioselective synthesis of biologically important 3-aryllawsones: scope and applications

A. V. Krishna and D. B. Ramachary, Org. Biomol. Chem., 2022, 20, 3948 DOI: 10.1039/D2OB00438K

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