A novel synthetic approach to pyran-2,4-dione scaffold production: Microwave-assisted dimerization, cyclization, and expeditious regioselective conversion into β-enamino-pyran-2,4-diones

[Display omitted] •A novel synthetic approach to pyran-2,4-dione scaffold.•Microwave-assisted dimerization, and cyclization to afford pyran-2,4-dione.•Expeditious regioselective conversion β-diketone systems into β-enamino-pyran-2,4-diones.•Novel cyclized compound 24 was achieved.. Here, we report a...

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Veröffentlicht in:Tetrahedron letters 2020-12, Vol.61 (52), p.152660, Article 152660
Hauptverfasser: Sarhan, Ahmed A.M., Haukka, Matti, Barakat, Assem, Boraei, Ahmed T.A.
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Sprache:eng
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Zusammenfassung:[Display omitted] •A novel synthetic approach to pyran-2,4-dione scaffold.•Microwave-assisted dimerization, and cyclization to afford pyran-2,4-dione.•Expeditious regioselective conversion β-diketone systems into β-enamino-pyran-2,4-diones.•Novel cyclized compound 24 was achieved.. Here, we report a novel, green, simple, low-cost, and rapid methodology for the high-yield production of pyran-2,4-dione scaffolds under microwave irradiation. Regio- and stereoselective conversions of β-diketone systems into β-enaminones were achieved using 18 primary amines and four amino acid esters. Microwave-assisted further cyclization of 3-(β-substitutedvinyl)-6-phenyl-pyran-2,4-dione into 3-benzoyl-4,7-diphenyl-2H,5H-pyrano[4,3-b]pyran-2,5-dione via reaction with ethyl benzoyl acetate.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2020.152660