Synthesis of Benzopyran-Fused Flavone Derivatives via Microwave-Assisted Intramolecular C–H Activation

Zoltán Sipos; Krisztina Kónya

doi:10.1055/s-0036-1591773

Synthesis, Table of Contents

Synthesis 2018; 50(08): 1610-1620
DOI: 10.1055/s-0036-1591773

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Synthesis of Benzopyran-Fused Flavone Derivatives via Microwave-Assisted Intramolecular C–H Activation

Zoltán Sipos

Department of Organic Chemistry, University of Debrecen, 4002 POB 400, Debrecen, Hungary Email: konya.krisztina@science.unideb.hu

,

Krisztina Kónya *

Department of Organic Chemistry, University of Debrecen, 4002 POB 400, Debrecen, Hungary Email: konya.krisztina@science.unideb.hu

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Abstract

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Dedicated to the memory of Prof. Tamás Patonay

Abstract

A microwave-assisted intramolecular direct arylation method for the synthesis of benzopyran-fused flavone derivatives containing natural flavone backbones is described. Different polyalkoxy flavones were synthesized and functionalized with 2-bromobenzyl bromide. The resulting compounds were subjected to palladium-catalyzed intramolecular direct arylation reactions supported by microwave irradiation to produce fused tetracyclic flavones. In the case of the 7-substituted chrysin derivative, the regioselectivity of the coupling was also examined.

Key words

flavones - C–H bond activation - palladium - intramolecular direct arylation - microwave chemistry

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References

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