A highly efficient metal-free selective 1,4-addition of difluoroenoxysilanes to chromones

A highly efficient metal-free selective 1,4-addition reaction of difluoroenoxysilanes to chromones was developed using the low-cost and readily available HOTf as the catalyst, which is a facile and straightforward method to access valuable C2-difluoroalkylated chroman-4-one derivatives. Interestingl...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2023-02, Vol.21 (5), p.133-137
Main Authors: Wang, Xi-Yu, Yang, Min, Zhou, Ying, Zhou, Jian, Hao, Yong-Jia
Format: Article
Language:English
Subjects:
Cancer
Catalysts
Chromones - chemistry
Chromones - pharmacology
HCT116 Cells
Humans
Lead
Lead compounds
Natural products
Optimization
Structure-Activity Relationship
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Summary:A highly efficient metal-free selective 1,4-addition reaction of difluoroenoxysilanes to chromones was developed using the low-cost and readily available HOTf as the catalyst, which is a facile and straightforward method to access valuable C2-difluoroalkylated chroman-4-one derivatives. Interestingly, the products could be readily converted to the difluorinated bioisostere of the natural product ( S )-2,6-dimethylchroman-4-one and a difluorinated benzo-seven-membered heterocycle via the Schmidt rearrangement reaction. In addition, the in vitro anti-proliferative activities of these synthesized derivatives against human colon carcinoma cells (HCT116) revealed that compound 3g exhibited potent inhibitory effect on HCT116 cancer cells with an IC 50 value of 6.37 μM, representing a novel lead compound for further structural optimization and biological evaluation. An efficient HOTf-catalyzed 1,4-addition reaction of difluoroenoxysilanes to chromones was developed, providing rapid access to valuable C2-difluoroalkylated chroman-4-ones. 3g showed antiproliferative effect on HCT116 cells with an IC 50 of 6.37 μM.
ISSN:1477-0520
1477-0539
DOI:10.1039/d2ob02152h