Collect. Czech. Chem. Commun.
2011, 76, 1255-1261
https://doi.org/10.1135/cccc2010150
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
Abstract
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 3a–3h in the presence of solid NaOH in CH2Cl2 resulted in the formation of the mixture of bicyclic lactone derivatives 5a–5h and 6-(ethoxycarbonyl)cyclohexenone derivatives 6a–6h.
Keywords: Chalcone; Ethyl acetoacetate; Cyclization; Lactonization; Cyclohexenones; Lactones; Cycloaddition.
References: 15 live references.
