Synthesis of cyclic sulfamides via one pot alkylation/aza-Michael cascade reaction.

[Display omitted] • • A transition metal-free strategy for the synthesis of cyclic sulfamides was developed. • • Orthogonal deprotection and side chain post-modification via a saponification/amide coupling sequence were implemented. • • The synthesized compounds showed inhibitory activity against human carbonic anhydrase isoform II (hCA II). A straightforward and transition metal-free method for the synthesis of cyclic sulfamides via base-promoted bis-alkylation of tert -butyl (N -alkylsulfamoyl)carbamates with electron-deficient allyl bromides is described. All obtained cyclic sulfamides underwent successful removal of tert -butoxycarbonyl protecting group. [ABSTRACT FROM AUTHOR]