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REDUCTIVE REARRANGEMENT OF 2-AROYL-2,3-DIHYDROBENZOFURANS INTO 2-HYDROXYDIHYDROCHALCONES AND FLAV-2-ENES

Дмитрий В. Осипов, Максим Р. Демидов, Виталий А. Осянин, Юрий Н. Климочкин
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Abstract


A two-step procedure was proposed for the synthesis of 2-aryl- and 2,4-diaryl-substituted 4H-chromenes by the formal [4+1] cycloaddition reaction of o-quinone methides and pyridinium ylides followed by reductive rearrangement of 2-aroyl-2,3-dihydrobenzofurans by the action of zinc in acetic acid or samarium and trimethylchlorosilane in 1,4-dioxane. The reduction of 3-unsubstituted 2aroyl-2,3-dihydrobenzofurans by the action of zinc in acetic acid leads mainly to 2-hydroxydihydrochalcones.

 


Keywords


2-aroyl-2,3-dihydrobenzofurans; 4H-chromenes; flav-2-enes; 2-hydroxydihydrochalcones; o-quinone methides; samarium; zinc; reductive rearrangement.

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