G. Hartman, W. Halczenko
Feb 1, 1990
Citations
0
Influential Citations
11
Citations
Journal
Journal of Heterocyclic Chemistry
Abstract
Novel 4-arylsulfonylthiophene- and furan-2-sulfonamides are prepared from the 3-arylsulfonyl heterocycle via chlorosulfonation with chlorosulfonic acid/phosphorus pentachloride. Free radical bromination affords bromomethyl analogues that are precursors to amine derivatives of the parent thiophenesulfonamides. Instability of the furansulfonyl chlorides to free radical bromination necessitated a sequence employing bromomethyl group generation prior to chlorosulfonation. Demethylation of methoxyl substituted sulfonamides afforded phenols that underwent efficient mono- and bis-alkylation with Mannich reagents.