Previous research by Dr. Murray Zanger (Emeritus, USP) has shown that tetrahydroquinoline sulfones and sulfonamides possess some anti HIV-1 activity. The synthesis of other five, six and seven membered benzo-fused heterocyclic sulfonamides and sulfones as potential anti-HIV agents are now being investigated by our research group. Indoline is a 5 membered nonaromatic benzo-fused heterocycle. Previous attempts have been successful in synthesizing the indoline p-toluene sulfonamide; however, efforts to rearrange the sulfonamide to a sulfone via a strong acid (H2SO4) have not been successful. Recently, it has been noted that indoline sulfonamides will rearrange to sulfones in a polyphosphoric acid medium. By utilizing this pathway for rearrangement, it should be feasible to synthesize a small library of compounds containing the indoline sulfonamide and sulfone moiety. Furthermore, any indoline compounds that are synthesized should be able to be aromatized (unsaturation of C2-C3 on pyrrole ring) into its indole counterpart. Indole is a 5 membered benzo-fused aromatic heterocycle whose structure is common to many binding sites in the human body. Indole compounds have been studied intensely for widespread pharmalogical uses such as anti-inflammatory agents, betablockers, and anti-Alzheimer agents. Another possible use of indole sulfonamide and sulfone derivatives is for anti-HIV activity as non-nuclease reverse transcriptase inhibitors (NNRTI). Indole sulfonamides can rearrange to indole sulfones by electrophilic sulfonation at the C3 position on the pyrrole ring of the indole nucleus. Indole sulfonamides undergo rearrangement to indole sulfones in polyphosphoric acid media as well as sulfuric acid in smaller yield. Using the aid of blocking groups on the C2 and C3 carbons should allow for addition of substitution to the benzene ring. Once the benzene ring has been successfully substituted, the blocking groups can be removed to produce new novel indole sulfones and sulfonamides.