Benzo[b]thiophene derivatives. XXI. On the proof of structure of the sulfur isostere of psilocin

AbstractDifferences in the characteristics of several common compounds reported in two independent syntheses of the sulfur analog of psilocin required re-examination of our products. Additional evidence supporting the structures previously reported by us is presented. This includes proof of 3-substitution in 4-methoxy-3-β-dimethylaminoethylbenzo[b]thiophene by deuterium exchange of the 2-proton, demonstration that the intermediate 4-methoxy-N, N-dimethyl-3-benzo[b]thienylglyoxamide is different from the 2-isomer, and confirmation of the structure of 4-methoxy-3-methylhenzo[b]thiophene, an intermediate in one of the reported syntheses, by three different synthetic methods.