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A convenient synthesis of quinoline fused triazolo-azepine/oxepine derivatives through Pd-catalyzed C-H functionalisation of triazoles

Abstract

An efficient and convenient synthesis of new fused heterocyclic scaffold comprising three different heterocycles viz. quinoline,azepine/oxepine and triazoleis reported from quinoline tethered triazoles. The quinoline tethered triazoles were easily obtained in three steps from 2-chloro-3-formylquinolines,that is, reductive amination with benzyl amines, N-propargylation followed by ‘click’ reaction under standard conditions. For the first time, we present quinoline fused triazolo-azepines in good to high yields by palladium-catalysed C-H functionalisation at C-5position of triazole moiety. The protocol readily extended even to the construction of quinoline fused triazolo-oxepines from (2-chloroquinolin-3-yl)methanol through the similar sequence,that is, O-propargylation,click reaction and palladium catalysedC-H functionalisation.

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Supplementary files

Article information


Submitted
19 Oct 2019
Accepted
07 Jan 2020
First published
08 Jan 2020

New J. Chem., 2020, Accepted Manuscript
Article type
Paper

A convenient synthesis of quinoline fused triazolo-azepine/oxepine derivatives through Pd-catalyzed C-H functionalisation of triazoles

M. Kukkamudi, R. Kanakaraju , P. K. Rathod and L. Panaganti, New J. Chem., 2020, Accepted Manuscript , DOI: 10.1039/C9NJ05254B

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