Issue 92, 2016, Issue in Progress

nBu4NPF6 promoted regioselective cascade synthesis of functionally embellished naphthofurans under acid, metal & solvent free conditions

Abstract

n Bu4NPF6 mediated highly regioselective synthesis of functionally embellished naphthofurans has been achieved from easily available naphthols and propargyl alcohols through a cascade benzylation, oxacyclisation (5-exo dig) and isomerization under solvent free conditions. The reaction works in a short time through dibenzyl ether formation followed by the decomposition to the carbocation to furnish the high yielding products with large substrate scope. The synthetic utility of the products is demonstrated through C(sp3)–H functionalization. In addition, we investigated selected naphthofurans for their anti-amyloidogenic properties. Preliminary studies suggest that these are excellent inhibitors for amyloid formation, a hallmark for several neurodegenerative diseases.

Graphical abstract: nBu4NPF6 promoted regioselective cascade synthesis of functionally embellished naphthofurans under acid, metal & solvent free conditions

Supplementary files

Article information

Article type
Paper
Submitted
07 Jul 2016
Accepted
12 Sep 2016
First published
13 Sep 2016

RSC Adv., 2016,6, 89732-89743

n Bu4NPF6 promoted regioselective cascade synthesis of functionally embellished naphthofurans under acid, metal & solvent free conditions

A. Pareek, R. Dada, M. Rana, A. K. Sharma and S. Yaragorla, RSC Adv., 2016, 6, 89732 DOI: 10.1039/C6RA17411F

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