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
Sarhan, A. A., Haukka, M., Barakat, A., & Boraei, A. T. (2020). 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. Tetrahedron Letters, 61(52), Article 152660. https://doi.org/10.1016/j.tetlet.2020.152660
Published inTetrahedron Letters
DisciplineEpäorgaaninen kemiaEpäorgaaninen ja analyyttinen kemiaInorganic ChemistryInorganic and Analytical Chemistry
Embargoed until: 2023-01-01Request copy from author
© 2020 Elsevier
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.
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Additional information about fundingThe authors would like to extend their sincere appreciation to the Researchers Supporting Project Number (RSP-2020/64), King Saud University, Riyadh, Saudi Arabia.
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