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Synthesis
DOI: 10.1055/a-2356-8347
DOI: 10.1055/a-2356-8347
paper
Special Topic Dedicated to Prof. H. Ila
Harnessing the Reactivity of ortho-Alkynylaldehydes: Silver Triflate Catalyzed Regioselective Synthesis of Phosphonylated Fluorescent Molecules
The research work was funded by Science and Engineering Research Board (CRG/2022/008887) and IoE/2021/12/FRP.
Dedicated in Honor of Prof. H. Ila
Abstract
An efficient approach for the facile synthesis of phosphonylated 1,3-dihydrofuro[3,4-b]quinolines and dihydrofuro[3,4-b]pyridines is developed. Reaction proceeds by the formation of new C–P and C–O bonds affording Z-selective phosphonylated products at room temperature. Diphenylphosphine oxides and dialkyl phosphites are explicitly incorporated into the carbonyl carbon of o-alkynylaldehydes in good to excellent yields. The reaction exhibits mild conditions, broad substrate scope, and the formation of three new bonds in the presence of a silver catalyst. The mechanistic studies revealed that the reaction proceeded via an ionic pathway in a 5-exo-dig manner to give Z-selective products, which was validated by X-ray crystallographic studies. Photophysical studies of selected compounds revealed the emission maxima in the range of 455 nm.
Key words
diphenylphosphine oxide - o-alkynylaldehydes - 1,3-dihydrofuro[3,4-b]quinolines - alkynes - phosphonylatedSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2356-8347.
- Supporting Information
Publikationsverlauf
Eingereicht: 22. Mai 2024
Angenommen nach Revision: 27. Juni 2024
Accepted Manuscript online:
28. Juni 2024
Artikel online veröffentlicht:
22. Juli 2024
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