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Electronic effects on a one-pot aromatization cascade involving alkynyl-Prins cyclization, Friedel–Crafts alkylation and dehydration to tricyclic benzo[f]isochromenes

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Abstract

A three-step domino reaction between 1-aryl-3-hexyne-2,6-diol derivatives and aldehydes is used to construct tricyclic 1,4-dihydro-2H-benzo[f]isochromenes. The cascade is initiated by BF3·OEt2 and involves alkynyl-Prins cyclization, Friedel–Crafts alkenylation, and dehydration/aromatization to create a new, central aromatic ring and eliminate 2 equiv. of water. Electron-donating substituents on the aryl ring of the 1-aryl-3-hexyne-2,6-diols significantly increase overall yields as do electron-rich aldehyde reaction partners. For 2,4-disubstituted 2H-benzo[f]isochromene products, diastereoselectivities in the alkynyl-Prins reaction are ∼1.4 : 1 in favor of the cis-diastereomer. The stereochemistry of one cis-product was verified by X-ray crystallographic analysis and a second structure was also verified by X-ray analysis.

Graphical abstract: Electronic effects on a one-pot aromatization cascade involving alkynyl-Prins cyclization, Friedel–Crafts alkylation and dehydration to tricyclic benzo[f]isochromenes

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Publication details

The article was received on 10 Jun 2017, accepted on 10 Aug 2017 and first published on 11 Aug 2017


Article type: Paper
DOI: 10.1039/C7OB01412K
Citation: Org. Biomol. Chem., 2017, Advance Article
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    Electronic effects on a one-pot aromatization cascade involving alkynyl-Prins cyclization, Friedel–Crafts alkylation and dehydration to tricyclic benzo[f]isochromenes

    R. J. Hinkle, Y. Chen, C. P. Nofi and S. E. Lewis, Org. Biomol. Chem., 2017, Advance Article , DOI: 10.1039/C7OB01412K

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