Saturated heterocyclic compounds containing two heteroatoms are privileged scaffolds for various pharmaceuticals. Among them, S,N-heterocyclic molecular scaffolds appear to be useful in designing potent antipsychotic (e.g. Quetiapine), antiarrhythmic (e.g. Diltiazem), anti-tumor (e.g. Prinomastat) and other biologically active agents [1]. Therefore, they remain to be important synthetic targets.
A collection of valuable (un)substituted N-protected cyclic eight-membered C2-symmetric sulfenamides, 1,5,2,6-dithiadiazocanes, has been prepared in few steps from cheap and affordable starting materials. The synthetic utility of these ambipolar derivatives was demonstrated in a variety of synthetic transformations affording different S,N-heterocycles of pharmaceutical relevance (Fig. 1).
