301. Synthesis and characterization of novel indanone-based spiro-dihydrobenzofuran derivatives
- Author
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Meliha Burcu Gürdere, Yakup Budak, Mustafa Ceylan, Neşe Dürü, Gaziosmanpaşa Üniversitesi, and 0-Belirlenecek
- Subjects
Kimya, Organik ,010405 organic chemistry ,Indanone,spirobenzofuran,chalcone-like compound,Mn(OAc)$_{3}$,dimedone ,Kimya, İnorganik ve Nükleer ,General Chemistry ,010402 general chemistry ,Kimya, Uygulamalı ,01 natural sciences ,Medicinal chemistry ,Kimya, Analitik ,Mühendislik, Kimya ,0104 chemical sciences ,Characterization (materials science) ,Benzaldehyde ,chemistry.chemical_compound ,Column chromatography ,chemistry ,Elemental analysis ,Dimedone ,Indene ,Spirobenzofuran ,Spectral data ,Kimya, Tıbbi - Abstract
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-1$H$-inden-1-one derivatives, were synthesized by the base-catalyzed addition of benzaldehyde derivatives to 2,3-dihydro-1$H$-inden-1-one. Then Mn(OAc)$_{3}$-mediated addition of dimedone (2) to the chalcone-like compounds gave two novel spiro-dihydrobenzofuran isomers: (3$S)$-6,6-dimethyl-3-aryl-6,7-dihydro-3$H$-spiro [benzofuran-2,2'-indene]-1',4(3'$H$,5$H)$-dione (5a-k) and (2'$S)$-6,6-dimethyl-2-aryl-6,7-dihydro-2$H$-spiro[benzofuran-3,2'-indene]-1',4(3'$H$,5$H)$-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.