ORGN 622 |
| Hui Ren, Murray Zanger, and James R McKee. Department of Chemistry and Biochemistry, University of the Sciences in Philadelphia, 600 South 43rd Street, Philadelphia, PA 19104 |
| N-Alkyl arylsulfonamides have been shown to rearrange to diarylsulfones (e.g. N-Methyl-N-phenylbenzenesulfonamide to N-Methyl-N-[2-(phenylsulfonyl)phenyl]amine) in the presence of 98% sulfuric acid. Research carried out in this laboratory found that cyclic aryl aminesulfonamides (e.g. 1-phenylsulfonyl 1,2,3,4-tetrahydroquinoline) also underwent this rearrangement. The product sulfones were shown to have significant anti-HIV activity. When the rearrangement was tried with the 5-membered amine analogue (the phenylsulfonylindoline), only cleavage of the sulfonamide was observed. The current project was undertaken to prepare the sulfonamide of the seven-membered analogue (tetrahydrobenzazepine) and to determine whether it underwent rearrangement or cleavage when treated with concentrated sulfuric acid. Results revealed that the seven-membered benzazepine sulfonamide also underwent rearrangement to give two isomers 9-[(2-nitrophenyl)sulfonyl]-2,3,4,5-tetrahydro-1H-1-benzazepine and 7-[(2-nitrophenyl)sulfonyl]-2,3,4,5-tetrahydro-1H-1-benzazepine. Several aryl ring substituted compounds will be synthesized and evaluated for their anti-HIV activity. |
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New Reactions, Methodology, Heterocycles, Aromatics
8:00 PM-10:00 PM, Wednesday, August 25, 2004 Pennsylvania Convention Center -- Hall D, Poster
Division of Organic Chemistry |