Spirocyclic β-oxo sulphoxides and sulphones as potential aldose reductase inhibitors

Abstract

Two isomeric five-membered spirocyclic β-oxo sulphones (4c) and (5), based on the 6-fluorochroman nucleus, have been prepared. The diastereoisomeric sulphoxides (4d) and (4e) corresponding to (4c) were also prepared. In addition, a related six-membered β-oxo sulphoxide (6b) of a spirocyclic 1,3-dithiane has been synthesized. In this case the corresponding sulphone was unstable under the reaction conditions. These compounds were prepared as potential aldose reductase inhibitors but were found to be devoid of this activity.