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Synthesis and derivatization of 4‐arylsulfonylthiophene‐ and furan‐2‐sulfonamides
Author(s) -
Hartman George D.,
Halczenko Wasyl
Publication year - 1990
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570270202
Subject(s) - chemistry , halogenation , furan , reagent , alkylation , demethylation , amine gas treating , derivatization , organic chemistry , phenols , moiety , sulfonamide , combinatorial chemistry , catalysis , biochemistry , gene expression , high performance liquid chromatography , dna methylation , gene
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.