T. Grimaldi, D. Back, G. Zeni
Oct 11, 2013
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0
Influential Citations
19
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Journal
The Journal of organic chemistry
Abstract
We present here our results on potassium tert-butoxide promoted annulation reactions of 2-alkynylphenyl propargyl ethers to give two different types of heterocycles: 3-benzyl-2-alkynylbenzofurans and 12H-benzoannulenbenzo[b]furans. A series of functionalized 2-alkynylphenyl propargyl ethers were efficiently cyclized by potassium tert-butoxide to the corresponding products. The optimized reaction conditions tolerated a large variety of functional groups, including electron-rich, electron-poor, and N-heterocyclic substrates. Selective product formation was obtained by controlling the solvent and temperature. When THF was used at room temperature, 3-benzyl-2-alkynylbenzofuran derivatives were exclusively obtained, while the use of DMF at 60 °C gave selectively 12H-benzoannulen[b]benzofurans.