Investigations in the rearrangements of sulfonanilides to diaryl sulfones

ORGN 720

Lisa Marie Neuls Meseroll,, James R McKee,, and Murray Zanger. Department of Chemistry and Biochemistry, University of the Sciences in Philadelphia, 600 S. 43rd Street, Philadelphia, NJ 19104
Previous work in this laboratory revealed that tetrahydroquinoline sulfones are effective non-nucleoside reverse transcriptase inhibitors of HIV-1. In this laboratory, rearrangement of cyclic aryl aminesulfonanilides to diaryl sulfones in the presence of concentrated acid has provided a convenient one-step route to the sulfones. Until recently, only concentrated sulfuric acid was effective as the rearrangement catalyst. Successful rearrangements of dihydroindole sulfonamides to sulfones by polyphosphoric acid (not accessible via sulfuric acid) indicated effects of different acid catalysts in these rearrangements.

In hopes of further expanding our knowledge of rearrangements, a variety of acid catalysts were tested via the rearrangement of 5,6-dihydrophenanthridine sulfonamides to their derivative sulfones. Currently, a panel of new 5,6-dihydrophenanthridine sulfonamides and their corresponding diaryl sulfones is being synthesized. All new compounds will be sent out for testing of inhibitory activity against HIV-1.