An Efficient Aromatization of 2-Amino-4,5,6,7-tetrahydrobenzo-[b]thiophene-3-carboxylates in Dimethyl Sulfoxide Catalyzed by p-Toluenesulfonic Acid

作者：Adib Mehdi^*; Soheilizad Mehd; Rajai daryasaraei Saideh; Mirzaei Peiman

来源：Synlett, 2015, 26(8): 1101-1105.

DOI：10.1055/s-0034-1379998

• 2-aminobenzo[b]thiophene-3-carboxylates
• Gewald reaction
• oxidation-aromatization
• dimethyl sulfoxide
• p-toluenesulfonic acid

A novel oxidation-aromatization of alkyl 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylates is reported. The Gewald product, obtained from three-component condensation reaction between a cyclohexanone, an alkyl cyanoacetate, and sulfur, underwent an oxidation reaction in dimethyl sulfoxide in the presence of a catalytic amount of p-toluenesulfonic acid to give the corresponding alkyl 2-aminobenzo[b]thiophene-3-carboxylate in excellent yield.

• 出版日期2015-5