Synthesis of tricyclic compounds with sulfur and silicon heteroatoms in the central ring

Abstract

The synthesis of tricyclic derivatives which contain both silicon and sulfur in a central six-, seven- and eight-membered ring are described. Phenothiasilin-5,5-dioxides are prepared by treatment of ( o-LiC 6H 4) 2SO 2 with dichlorosilanes. Reduction of the sulfone group is described as well as attempts to introduce aminopropyl substituents at silicon. Thiasilepins are prepared from the Grignard reagent of ( o-BrC 6H 4CH 2SC 6H 4Br- o) and reactions of this ring system are described. Reaction of Me 2Si(C 6H 4CH 2Br- o) with Na 2S gave a thiasilocin derivative.