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• W2953579532 abstract "A general synthetic route to the unknown 1,3‐dicarbonyl tropane derived curcumin analogues was developed. The method was based on the aldol condensation reaction (40–90 % yield, two steps without product isolation) and acylation of the resulting 2‐benzylidenetropinones with substituted cinnamoyl cyanides (yields 41–91 %). Overall 18 new tropane derivatives featuring the characteristic curcuminoid hepta‐1,6‐dien‐3,5‐dione structure were synthesized and characterized. The range of the substituted aromatic rings in the prepared analogues included Ph, m ‐MeO‐C 6 H 4 , 3,4‐di‐MeO‐C 6 H 3 , 3,4,5‐tri‐MeO‐C 6 H 2 , p ‐Br‐C 6 H 4 , p ‐F‐C 6 H 4 , p ‐CF 3 ‐C 6 H 4 , p ‐NO 2 ‐C 6 H 4 , 2‐NO 2 ‐4,5‐di‐CH 3 O‐C 6 H 2 , 2‐NO 2 ‐4,5‐O‐CH 2 ‐O‐C 6 H 2 , 3‐MeO‐4‐[CH(CH 3 )‐OEt]‐C 6 H 3 , 3‐MeO‐4‐OH‐C 6 H 3 , p ‐MeO‐C 6 H 4 , 4,5‐O‐CH 2 ‐O‐C 6 H 3 , 3‐MeO‐4‐MeOCOO. Two orthogonal protective groups for hydroxyl (acetal or carbonate), removable in acidic or basic conditions, were used for synthesizing curcuminoids with free phenolic groups (3‐MeO‐4‐OH‐C 6 H 3 )." @default.
• W2953579532 created "2019-07-12" @default.
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• W2953579532 date "2019-07-17" @default.
• W2953579532 modified "2023-10-14" @default.
• W2953579532 title "Synthesis of Dicarbonyl Curcumin Analogues Containing the Tropane Scaffold" @default.
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• W2953579532 doi "https://doi.org/10.1002/ejoc.201900416" @default.
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