Ultrasound-enhanced one-pot synthesis of 3-(Het)arylmethyl-4-hydroxycoumarins in water

Ultrason Sonochem. 2011 Mar;18(2):652-60. doi: 10.1016/j.ultsonch.2010.08.009. Epub 2010 Aug 18.

Abstract

3-(Aryl)methyl-4-hydroxycoumarins were produced in good to excellent yields by reaction between 4-hydroxycoumarin and (hetero)aromatic aldehydes in the presence of Hantzsch 1,4-dihydropyridine (HEH) which works as an hydride donor (i.e., in a sequential Knoevenagel-reductive Michael addition). The sonochemical-assisted procedure (method B) provides an improved and accelerated conversion when compared to conventional silent reactions (method A). Experiments carried out according to method B showed that the reaction could be more efficiently run in the absence of organic solvents, at 30-40°C in open vessel, without the need of an excess HEH and with simplified work-up and separation procedures.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzenesulfonates / chemistry
  • Coumarins / chemical synthesis*
  • Coumarins / chemistry*
  • Dihydropyridines / chemistry
  • Sonication*
  • Surface-Active Agents / chemistry
  • Water / chemistry*

Substances

  • Benzenesulfonates
  • Coumarins
  • Dihydropyridines
  • Surface-Active Agents
  • Water
  • dodecylbenzenesulfonic acid
  • 1,4-dihydropyridine