A Three-Component Novel Synthesis of 1-[Aryl(Thioacetamido)Methyl]-2-Naphthol Derivatives

Abstract

A three-component reaction between 2-naphthol, an aryl aldehydes and thioacetamide catalysed by p-toluenesulfonic acid under reflux conditions provided a simple and efficient one-pot route for the synthesis of 1-[aryl(thioaceta mido)methyl]-2-naphthol derivatives in excellent yields.

Highly Efficient Synthesis of 1-Thioamidoalkyl-2-naphthols and 14-Aryl-14H-dibenzo[a,j]xanthenes using a Novel Ionic Liquid: Catalyst Preparation, Characterization and Performing the Reactions

“…In a plausible mechanism (Scheme 3), which supported by the literature [19,23,24] is added to it to give the respective 1-thioamidoalkyl-2-naphthol.…”

“…A mixture of arylaldehyde (1 mmol), 2-naphthol (1 mmol), thioacetamide (1.2 mmol) and [TEASA][TFA] (0.044 g, 0.15 mmol) was firstly stirred by a magnet at 80 °C, and after solidification of the reaction mixture, it was stirred with a small rod at the same temperature. The progress of the reaction was monitored by TLC) n-hexane/ethyl acetate: 3/1); after completion of the reaction, the mixture was cooled to room temperature, and recrystallized from hot ethanol (95%) to give the pure product [18][19][20][21][22][23][24][25].…”

“…The 1-thioamidoalkyl-2-naphthol derivatives are of significance as they can be readily converted to biologically important compounds namely γ-amino alcohols which show hypotensive, bradycardia, antipain, antibacterial, secretase inhibitory and notch-sparing activities [14][15][16][17]. The general method for synthesis of 1-thioamidoalkyl-2-naphthols involves the condensation reaction of arylaldehydes with 2-naphthol and thioacetamide in the presence of a catalyst [18][19][20][21][22][23][24][25]. In spite of high importance of this class of compounds, their production has been scarcely studied in the literature.…”