Progresses in the Preparation of Chromone Compounds and Their Applications in Organic Synthesis

doi:10.6023/cjoc202403025

Abstract

Chromone is the core backbone of flavonoids and its derivatives have different applications. Meanwhile, the α,β-unsaturated ketone structure contained in chromones enables them to undergo reactions such as substitution, cyclization, and asymmetric addition, which promotes the generation of a variety of functionalized chromone analogues or other backbone molecules. Therefore, in addition to chromone natural products, the preparation of chromones and their use as synthons in organic synthesis applications are also of great interest. The preparation methods of chromones are summarized and the recent applications of important chromone synthons in organic synthesis are reviewed on the basis of reaction types and reaction regions.

Key words: chromones, synthons, functionalization, addition reaction

Cite this article

Zhonghao Li, Yu Zeng, Yong Zeng, Wenjin Xu, Xiying Cao, Yuting Guo, Qing Shen, Zhaoyang Wang. Progresses in the Preparation of Chromone Compounds and Their Applications in Organic Synthesis[J]. Chinese Journal of Organic Chemistry, 2024, 44(11): 3345-3356.

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Fig. & Tab. 14

Scheme 1. Synthesis and reaction mechanism of 3-acylchromone 3

Scheme 2. Internal cyclization of ketene dithioacetals 5 and their one-pot reaction

Scheme 3. Synthesis of chromones from aromatic aldehydes and halogenated olefins

Scheme 4. Cross-dehydrogenative coupling of chromone with polyfluorinated alcohol

Scheme 5. Regioselective sulfenylation of chromones

Scheme 6. Synthesis of 2,3-disubstituted chromone derivatives from 3-iodochromone

Scheme 7. Direct regioselective selenylation of chromones at the C(5)-position under Ru(II) catalysis

Scheme 8. Palladium-catalyzed cyclization of 3-iodochromone with NBE and o-bromobenzoic acid

Scheme 9. Palladium-catalyzed cyclization of 3-iodochromones with different components

Scheme 10. Construction of highly functionalized bispiro[benzofuran-oxindole/benzofuran-chromanone]s

Scheme 11. Lewis acid-catalyzed benzannulation of vinyloxiranes with 3-formylchromones

Scheme 12. Different substituents control the ring-opening or fused cyclization of 3-substituted chromones

Scheme 13. Synthesis of dicyanomethylene-benzopyran derivatives and fluorescent probes via chromones

Scheme 14. Synthesis of fluorescent probes 22 via chromones

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