A simple approach to highly functionalized benzo[b]furans from phenols and aryl iodides via aryl propargyl ethers |
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| Authors: | V.S. Prasada Rao Lingam Ramanatham Vinodkumar Abraham Thomas |
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| Affiliation: | a Glenmark Research Centre, Medicinal Chemistry Division, MIDC Mahape, Navi Mumbai 400 709, India
b Institute of Science and Technology, Jawaharlal Nehru Technological University, Kukatpally, Hyderabad 500 072, India |
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| Abstract: | A variety of mono- and disubstituted phenols are alkylated with propargyl bromide to give phenyl 2-propynyl ethers, which were further coupled with aryl iodides under Sonogashira reaction conditions to give 3-phenoxy-1-aryl-1-propyne derivatives. The latter compounds underwent an initial Claisen rearrangement followed by ring closure to give functionalized benzo[b]furans in moderate to good yields. |
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| Keywords: | Aryl propargyl ethers Benzo[b]furans Sonogashira coupling Claisen rearrangement |
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