Synthesis of 5H‐Selenopheno[3,2‐c]isochromen‐5‐ones Promoted by Dialkyl Diselenides and Oxone

We describe here for the first time the synthesis of isochromenones fused to selenophenes. 5H‐Selenopheno[3,2‐c]isochromen‐5‐ones were obtained through a double intramolecular cyclization of methyl 2‐(organyl‐1,3‐diynyl)benzoate promoted by electrophilic species of selenium generated in situ by the...

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Veröffentlicht in:Advanced synthesis & catalysis 2019-07, Vol.361 (14), p.3403-3411
Hauptverfasser: Goulart, Helen A., Neto, José S. S., Barcellos, Angelita M., Barcellos, Thiago, Silva, Márcio S., Alves, Diego, Jacob, Raquel G., Lenardão, Eder J., Perin, Gelson
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Sprache:eng
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Zusammenfassung:We describe here for the first time the synthesis of isochromenones fused to selenophenes. 5H‐Selenopheno[3,2‐c]isochromen‐5‐ones were obtained through a double intramolecular cyclization of methyl 2‐(organyl‐1,3‐diynyl)benzoate promoted by electrophilic species of selenium generated in situ by the reaction of dialkyl diselenides with Oxone®, using ethanol as solvent. The reactions were conducted satisfactorily under mild conditions, using a range of 1,3‐diynes and dialkyl diselenides as substrates. A total of sixteen unprecedent 5H‐selenopheno[3,2‐c]isochromen‐5‐ones were selectively obtained in moderate to good yields (40–86%) under reflux in an open flask and in short reaction times (1.0–2.5 h).
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201900288