Alternate synthesis of heterocyclic sulfones as medicinal compounds

ORGN 657

Kristen N Adams Barrett, kadams@mail.usp.edu, James McKee, and Murray Zanger. Department of Chemistry & Biochemistry, University of the Sciences in Philadelphia, 600 S. 43rd St, Philadelphia, PA 19104
Heterocyclic sulfones can be synthesized in a variety of ways including oxidation of sulfides or sulfoxides, from sulfonic acids or by a Fries rearrangement from sulfonanilides. Because the starting materials maybe difficult to obtain, the yield is often low and the positions of substitution are limited, we became interested in a simple direct synthetic route to substituted heterocyclic sulfones. We have found from previous work, halide sulfinic acid displacement with less activated halides through copper iodide catalyzed coupling and more activated halides through aromatic substitution to be the most successful. Current research involves developing a synthesis of various heterocyclic sulfinic acids. If this synthesis is successful a wide variety of currently unknown substituted sulfones could be produced from said methods and tested for medicinal properties.