Abstract

We here present a simple and efficient method for the preparation of 2-substituted-thiazolomorphinanedienes 3-5. A protocol is also presented for yielding 3-demethoxy-14β-hydroxy derivatives of the thiazolomorphianedienes. The amino-, methyl- and phenyl-substituents connected in these compounds in a less rigid way to the “spacer” which offers the opportunity to test the effect of this sterically more flexible structure on the activity to opioid receptor subtypes.

Keywords: Hantzsch-type thiazole synthesis, morphinanediene, O-demethylation, introduction of 14-hydroxyl-motif