The Synthesis Of A New Class Of Quinolinone Alkaloids And Its Application In Organic Synthesis

The design and synthesis of L-proline-catalyzed Aldol reaction with 4-hydroxy-3-acetyl--1-methyl-1H-quinolin-2-one and different kinds of aromatic aldehydes to give the new Chalcone analogous containing quinolin-2-one block were investigated, followed by the research interesting on the oxidative cyclization of these analogous to synthesis the new Flavonoides and the synthesis of new calixarene. It was found that L-proline is the better catalyst than KOH in Aldol reaction of 4-hydroxy-1-methyl-1H-quinolin-2-one with aromatic aldehydes to afforded the Chalcone analogous in moderate to good yields at room temperature. 4-hydroxy-l,methyl-3-(4-hydroxyl-benzophenone )-1H-quinolin-2-one, which get from 3-acetyl-4-hydroxy- 1-methyl- 1H-quinolin-2-one and 4-hydroxy-benzophenone, can be efficiently converted into corresponding Flavonoides via oxidative cyclization with PdCl₂-CuCl at O₂ atmosphere in above 80% yield. This cyclization can also be achieved by using PIDA or I₂ as the oxidant. The synthesis of the calixarene from one of Chalcone analogous with ormaldehyde was also investigated.