Synthesis of sultams by cycloalkylation of (alkoxycarbonylmethane) sulfonanilides

Article abstract of DOI:10.1007/s10593-008-0066-9

(Methoxycarbonylmethane)sulfonanilides are alkylated by α, ω-dihaloalkanes in K₂CO₃-DMF with the formation of sultams. A high sensitivity has been detected for the reaction rate on the electronic effect of substituents in the aromatic nucleus, although substituents in the ortho position do not obstruct the reaction and in the case of 2,6-disubstituted derivatives the reaction rate and sultam yield were maximal. Tertiary sulfonamides form derivatives of 1-sulfamoylcyclopropanecarboxylic acid under these conditions.