Simple synthesis of a new family of 22- to 28-membered macrocycles containing two chalcone moieties

Abstract

A new family of 22- to 28-membered tetrabenzo-macrocycles containing two chalcone moieties has been synthesized from 2-hydroxybenzaldehyde and 2'-hydroxyacetophenone through phenol alkylation with α,ω- dibromoalkanes followed by Claisen-Schmidt reaction under high dilution condition. All the compounds of this family were found to possess both the double bonds in E-configuration. An attempt to synthesize another family of isomeric tetrabenzo-macrocycles having opposite alignment of the two chalcone moieties by reaction of 2,2'-dihydroxychalcone with α,ω- dibromoalkanes was not successful, a series of 12- to 14-membered dibenzo-macrocycles with only one chalcone moiety was obtained here. ©ARKAT-USA, Inc.