A convenient method for the synthesis of 3-acetoxy-N,Ndialkylbenzo[b]thiophene-2-carboxamides has been developed in three steps from 2-ethylsulfanylbenzoates using an interrupted Pummerer reaction of N,N-dialkyl-3-(2-ethylsulfinylphenyl)-3-oxopropanamides. Thus, treatment of these sulfinyl amides, prepared by the reaction of 2-ethylsulfanylbenzoates with lithium enolates of N,N-dialkylacetamides followed by oxidation of the resulting N,Ndialkyl-3-(2-ethylsulfanylphenyl)-3-oxopropanamides with sodium metaperiodate and acetic anhydride at 100 °C leads to the formation of the desired benzo[b]thiophenes.

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Synthesis of 1,2,3,5-Tetrahydro-4,1-benzothiazepine-2-thione Derivatives via Cyclization of 2-[(2-Isothiocyanatophenyl)methylsulfanyl]acetates with SodiumHydride. -A convenient method for the synthesis of the title compounds (II), (IV), and (V) from readily available starting materials is presented. The use of EtBr instead of EtI (IIIb) in the synthesis of the compound (IVb) fails. The reaction of the (IIIb) with (Ia) to prepare the ethyl analogue of (V) also fails. -(KOBAYASHI*, K.; ENMI, Y.; IITSUKA, D.; KANBE, Y.; KONISHI, H.; Heterocycles 83 (2011 Heterocycles 83 ( ) 9, 2127 Heterocycles 83 ( -2135 Dep. Chem. Biotechnol., Grad. Sch. Eng.,