Issue 25, 2016

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

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

Supplementary files

Article information

Article type
Paper
Submitted
11 Apr 2016
Accepted
17 May 2016
First published
18 May 2016

Org. Biomol. Chem., 2016,14, 6065-6070

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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