Synthesis and structural characteristics of novel 5H-thiazolo[2,3-d][1,5]benzothiazepine derivatives

Abstract

The 5H-thiazolo[2,3-d][1,5]benzothiazepines 13–16 have been synthesized by condensation of the 1,5-benzothiazepine-2-thiones 5–8 and α-bromoacetaldehyde diethyl acetal followed by treatment with alkali. The structure and stereochemistry of the adducts obtained has been established on the basis of spectroscopic data. For compounds 15 and 16 the presence in solution of two conformers has been postulated. An X-ray crystallographic structural study of thiazolobenzothiazepine 15 reveals that only one conformer is present in the solid state, stabilized by the presence of a short S · · · O contact (2.59 Å).