Synthesis of 1H-pyrano[4,3-b]benzofuran-1-one derivatives via photochemical cyclization of substituted 4H-furo[3,2-c]pyran-4-ones

[Display omitted] •A new method for the synthesis of 1H-pyrano[4,3-b]benzofuran-1-ones was developed.•The process involve photochemical reaction of 4H-furo[3,2-c]pyran-4-ones.•Accessible starting materials, mild and environmentally friendly reaction conditions.•Typical structure was confirmed by X-r...

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Veröffentlicht in:Tetrahedron letters 2020-10, Vol.61 (44), p.152469, Article 152469
Hauptverfasser: Milyutin, Constantine V., Lichitsky, Boris V., Melekhina, Valeriya G., Komogortsev, Andrey N., Fakhrutdinov, Artem N., Minyaev, Mikhail E., Krayushkin, Michail M.
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Sprache:eng
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Zusammenfassung:[Display omitted] •A new method for the synthesis of 1H-pyrano[4,3-b]benzofuran-1-ones was developed.•The process involve photochemical reaction of 4H-furo[3,2-c]pyran-4-ones.•Accessible starting materials, mild and environmentally friendly reaction conditions.•Typical structure was confirmed by X-ray crystallographic analysis. A novel approach for synthesis of fused 1H-pyrano[4,3-b]benzofuran-1-ones was developed based on the photochemical reaction of 2,3-disubstitued 4H-furo[3,2-c]pyran-4-ones. The studied process includes the photocyclization of the hexatriene system and subsequent aromatization of benzene ring via elimination of water molecule. The structure of one of the 1H-pyrano[4,3-b]benzofuran-1-one derivatives was determined by X-ray diffraction.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2020.152469