Abstract
2, 6-Epithio-3-benzazocines (9-thiabenzomorphans) in which the carbon atom at the 11-position is replaced by a sulfur atom, were synthesized by treatment of 1-(2-ethoxycarbonylaminoethyl)isothiochroman asulfoxides (16) with acetic anhydride or by heating 3-acetoxyisothiochromans (17) in Dowtherm A.The hetero-acetal moiety of this novel heterocycle (15) was stable to lithium aluminum hydride and boron tribromide. Reduction of 15 with lithium aluminum hydride gave the N-methyl derivative (19) and demethylation of the 8-methoxy derivative (19b) with boron tribromide gave the 8-hydroxy derivative (20).
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