: NBu4NPF6 promoted regioselective cascade synthesis of functionally embellished naphthofurans under acid, metal & solvent free conditions

Abhishek Pareek, Ravikrishna Dada, Monika Rana, Anuj K. Sharma, Srinivasarao Yaragorla

Research output: Contribution to journalArticlepeer-review

25 Scopus citations

Abstract

nBu4NPF6 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.

Original languageEnglish (US)
Pages (from-to)89732-89743
Number of pages12
JournalRSC Advances
Volume6
Issue number92
DOIs
StatePublished - 2016
Externally publishedYes

Bibliographical note

Publisher Copyright:
© 2016 The Royal Society of Chemistry.

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