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Issue 4, 2020
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Ru-Catalyzed cascade reaction of α,ω-alkynoic acids and arylethylamines towards the synthesis of aryl-fused heterocycles

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Abstract

A simple, efficient, and mild method for the preparation of aryl-fused heterocycles has been developed using α,ω-alkynoic acids and arylethylamines. In the present method, one of Grubbs’ ruthenium carbenes is able to catalyze the formation of exocyclic enol lactones from α,ω-alkynoic acids, which subsequently undergo aminolysis and N-acyl iminium ion formation/cyclization with arylethylamines in the presence of TFA, affording one kind of “drug-privileged” scaffold. Demonstrated with high functional group tolerance, this new cascade reaction endows the Grubbs’ ruthenium carbene with a new synthetic utility beyond routine olefin metathesis.

Graphical abstract: Ru-Catalyzed cascade reaction of α,ω-alkynoic acids and arylethylamines towards the synthesis of aryl-fused heterocycles

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Article information


Submitted
16 Nov 2019
Accepted
10 Jan 2020
First published
13 Jan 2020

Org. Chem. Front., 2020,7, 660-665
Article type
Research Article

Ru-Catalyzed cascade reaction of α,ω-alkynoic acids and arylethylamines towards the synthesis of aryl-fused heterocycles

Y. Zheng, J. Liu and X. Lei, Org. Chem. Front., 2020, 7, 660
DOI: 10.1039/C9QO01375J

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