Action of Nitrogen and Carbon Nucleophiles on 6-Phenyl-3, 4-Dihydrocoumarin

Download this article as: 

3,4-Dihydro coumarin (1) reacted with aromatic aldehydes to give 3- arylidene derivatives <2a-d). The reaction of (1) with alkyl and/or aryl magnesium halides afforded the corresponding Chroman derivatives ( 3a-f). The base catalysed addition of (1) to acrylonitrile yielded the Michael adduct (4). Also, (1) condensed with hydrazine hydrate, phenylhydrazine, semicarbazide and primary aromatic amines namely benzylamine, g-tolnidine, p_toluidine, oc-naphthylamine, 2-aminopyridine and/ or p-aminoazobenzene to give the corresponding N-(substituted)-2-quinolinone derivatives (6a-i) respectively. Also bromination of (1) has been described.

Action; Nitrogen