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Synthesis 2019; 51(18): 3431-3442
DOI: 10.1055/s-0039-1690001
DOI: 10.1055/s-0039-1690001
paper
Synthesis and Transformation of 5-Acetyl-2-aryl-6-hydroxybenzofurans into Furanoflavanone Derivatives
The authors thank the University of South Africa and the National Research Foundation (NRF) in South Africa (NRF GUN: 118554) for financial support.Further Information
Publication History
Received: 22 March 2019
Accepted after revision: 13 June 2019
Publication Date:
28 June 2019 (online)
Abstract
Tandem palladium-catalyzed Sonogashira cross-coupling and heteroannulation of 3-bromo-2,4-dihydroxy-5-iodoacetophenone with arylacetylenes followed by the base-mediated Claisen–Schmidt aldol condensation of the intermediate 5-acetyl-2-aryl-7-bromo-6-hydroxybenzofurans with benzaldehyde derivatives afforded the corresponding linear 2-arylbenzofuranchalcone hybrids. The presence of the o-hydroxy-trans-α,β-unsaturated carbonyl moiety in the prepared furanochalcone hybrids facilitated acid-mediated cycloisomerization into the corresponding linear furanoflavanones. The structures of the prepared compounds were confirmed using a combination of spectrometric techniques complemented with single crystal XRD analysis.
Keywords
3-bromo-2,4-dihydroxy-5-iodoacetophenone - Sonogashira cross-coupling - furanochalcones - furanoflavanones - X-raySupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0039-1690001.
- Supporting Information
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