Collect. Czech. Chem. Commun. 2011, 76, 1255-1261
Published online 2011-09-26 22:29:19

Unexpected lactonization accompanying addition of ethyl acetoacetate to chalcones derived from 3-acetylthiophene

Yakup Budak* and Esra Findik

Department of Chemistry, Faculty of Arts and Sciences, Gaziosmanpasa University, 60250 Tokat, Turkey


Chalcone derivatives containing thiophene ring were prepared by the condensation of 3-acetylthiophene with aromatic aldehydes in excellent yields. The addition of ethyl acetoacetate to chalcone derivatives 3a3h in the presence of solid NaOH in CH2Cl2 resulted in the formation of the mixture of bicyclic lactone derivatives 5a5h and 6-(ethoxycarbonyl)cyclohexenone derivatives 6a6h.

Keywords: Chalcone; Ethyl acetoacetate; Cyclization; Lactonization; Cyclohexenones; Lactones; Cycloaddition.

References: 15 live references.