کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
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56593 | 47088 | 2011 | 4 صفحه PDF | دانلود رایگان |
Cerium-catalyzed C–C coupling of 1,3-dicarbonyl compounds with styrene derivatives and oxygen yielded compounds with a 1,4-dicarbonyl moiety after base induced Kornblum–DeLaMare fragmentation. Further conversion of these 1,4-diketones with primary amines in a bismuth-catalyzed reaction gave eight-membered ring lactams, which are a new and promising molecular scaffold for medicinal chemistry. Further derivatization was achieved by saponification of esters to their corresponding carboxylic acids and followed by amidation with primary amines with a coupling reagent. We furthermore investigated the synthesis of cogeners with an additional O, S, or N atom in the eight-membered ring, thus extending the diversity of our scaffold.
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Journal: Catalysis Today - Volume 159, Issue 1, 10 January 2011, Pages 96–99