|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.
Heterocycles and Aromatics, Asymmetric Reactions and Syntheses and Total Synthesis of Complex Molecules
7:00 PM-9:00 PM, Wednesday, August 19, 2009 Walter E. Washington Convention Center -- Ballroom C, Poster