A1 Journal article (refereed)
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 (2020)


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


JYU authors or editors


Publication details

All authors or editors: Sarhan, Ahmed A.M.; Haukka, Matti; Barakat, Assem; Boraei, Ahmed T.A.

Journal or series: Tetrahedron Letters

ISSN: 0040-4039

eISSN: 1873-3581

Publication year: 2020

Volume: 61

Issue number: 52

Article number: 152660

Publisher: Elsevier

Publication country: United Kingdom

Publication language: English

DOI: https://doi.org/10.1016/j.tetlet.2020.152660

Publication open access: Not open

Publication channel open access:

Publication is parallel published (JYX): https://jyx.jyu.fi/handle/123456789/72986


Abstract

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.


Keywords: organic compounds; chemical synthesis; microwaves

Free keywords: pyran-2,4-dione; microwave; β-enaminones; intramolecular cyclization


Contributing organizations


Ministry reporting: Yes

Reporting Year: 2020

JUFO rating: 1


Last updated on 2021-07-07 at 21:31