Indanones are structural motifs frequently used as synthetic precursors of several biologically active both natural and pharmaceuticals compounds. The indanone plays a pivotal role in the donepezil (Aricept) mediated acetylcholinesterase (ACh) inhibition. The classical way to achieve an indanone moiety is to perform a Friedel- Craft cyclization of aryl propionic acyl chloride or Meldrum’s acids. Some examples of cyclization starting from aryl propionic acids has been reported in the literature, but all the procedures need superacids catalysts  or drastic reaction conditions . Molecular modelling studies have suggested indanone derivatives, reporting an EWG group on the aromatic cycle, as promising ACh inihibitors. An efficient ultrasounds-assisted Friedel-Craft cyclization of inactivated aryl propionic acids is presented. Ultrasounds allow to use a low amount of acid with respect to the procedures reported in the literature and to perform the reaction at room temperature or under slight heating. A comparison between the reaction performed with or without sonication shows that ultrasounds reduce the reaction time and improve the reaction yield giving rise to a pure product even in the case of strongly inactivated starting materials.
|Titolo:||Ultrasounds mediated cyclization of aryl propionic acids: a new route towards indanones|
|Data di pubblicazione:||2011|
|Appare nelle tipologie:||4.2 Abstract in Atti di convegno|