Properties and reactions of substituted 1,2-thiazetidine 1,1-dioxides: Alkylation and acylation of 3-haloalkyl β-sultams and synthesis of bicyclic β-sultams

Article abstract of DOI:10.1002/ardp.19933260802

Alkylation of the 3-chloroethyl substituted β-sultam 1 with bromoacetates yields the N- and 3-substituted β-sultams 2; exchange of halogens affords esters 3. Reactions of 1 or of the analogues 8 with isocyanates make the carbamoyl derivatives 5, 6, and 9 available. While cyclization of 6 with n-BuLi in the presence of HMPT yields the bicyclic β-sultams 7, the analogous reaction of 9 failed. The bicyclic β-sultams 12 and 14 are obtained from 3-hydroxyalkyl β-sultams 11 and 13 and carbonyl compounds. None of the prepared β-sultams showed any antibacterial activity.