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Issue 38, 2016
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Palladium meets copper: one-pot tandem synthesis of pyrido fused heterocycles via Sonogashira conjoined electrophilic cyclization

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Abstract

An efficient step-economical tandem approach for the direct synthesis of pyrido fused indole, quinoline, benzofuran and benzothiophene derivatives using a bimetallic Pd/Cu catalytic system has been described. The three component reaction of o-halo aldehydes, alkynes and tert-butylamine leads to the synthesis of biologically active polyheterocycles. The present strategy involves the dual role of tert-butylamine and copper(I) in Sonogashira coupling followed by electrophilic cyclization through imine formation. The chemistry has been validated by X-ray crystallographic studies.

Graphical abstract: Palladium meets copper: one-pot tandem synthesis of pyrido fused heterocycles via Sonogashira conjoined electrophilic cyclization

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Supplementary files

Article information


Submitted
19 Jul 2016
Accepted
25 Aug 2016
First published
25 Aug 2016

Org. Biomol. Chem., 2016,14, 9063-9071
Article type
Paper

Palladium meets copper: one-pot tandem synthesis of pyrido fused heterocycles via Sonogashira conjoined electrophilic cyclization

S. Kumar, R. K. Saunthwal, T. Aggarwal, S. K. R. Kotla and A. K. Verma, Org. Biomol. Chem., 2016, 14, 9063
DOI: 10.1039/C6OB01539E

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