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Issue 25, 2016
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Synthesis of furo[3,2-c]coumarin derivatives using visible-light-promoted radical alkyne insertion with bromocoumarins

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Abstract

The synthesis of privileged structures, which are potent drug candidates, is an impetus for drug discovery. The construction of heterocyclic framework furo[3,2-c]coumarins using a visible-light promoted photoredox neutral coupling of 3-bromo-4-hydroxycoumarins with commercially available alkynes has been reported. These reactions can be carried out at room temperature under visible light irradiation with good chemical yields. This work presents 17 furocoumarins, 12 of which are new. Three of the newly synthesized compounds show potent cytotoxicity, and one shows moderate acetylcholinesterase inhibitory activity with IC50 values of 2.16 ± 0.13 μM.

Graphical abstract: Synthesis of furo[3,2-c]coumarin derivatives using visible-light-promoted radical alkyne insertion with bromocoumarins

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Publication details

The article was received on 11 Apr 2016, accepted on 17 May 2016 and first published on 18 May 2016


Article type: Paper
DOI: 10.1039/C6OB00768F
Org. Biomol. Chem., 2016,14, 6065-6070

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    Synthesis of furo[3,2-c]coumarin derivatives using visible-light-promoted radical alkyne insertion with bromocoumarins

    H. Zhou, X. Deng, Z. Ma, A. Zhang, Q. Qin, R. X. Tan and S. Yu, Org. Biomol. Chem., 2016, 14, 6065
    DOI: 10.1039/C6OB00768F

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