Yakup BUDAK, Neşe DÜRÜ, Meliha Burcu GÜDERE, Mustafa CEYLAN

Synthesis and characterization of novel indanone-based spiro-dihydrobenzofuran derivatives

In this study, the synthesis and characterization of novel indanone-based spiro-dihydrobenzofuran derivatives were examined. Firstly, chalcone-like compounds 4a–k, (E)-2-benzylidene-2,3-dihydro-1H -inden-1-one derivatives, were synthesized by the base-catalyzed addition of benzaldehyde derivatives to 2,3-dihydro-1H -inden-1-one. Then Mn(OAc) 3 -mediated addition of dimedone (2) to the chalcone-like compounds gave two novel spiro-dihydrobenzofuran isomers: (3S)-6,6-dimethyl-3-aryl-6,7-dihydro-3H -spiro [benzofuran-2,2’-indene]-1’,4(3’H ,5H)-dione (5a–k) and (2’S)- 6,6-dimethyl-2-aryl-6,7-dihydro-2H -spiro[benzofuran-3,2’-indene]-1’,4(3’H ,5H)-dione (6a–k) in good yields. The isomers were separated by column chromatography and their structures were elucidated on the basis of spectral data (NMR, IR) and elemental analysis.

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