PROPERTIES AND REACTIONS OF SUBSTITUTED 1,2-THIAZETIDINE 1,1-DIOXIDES - ALKYLATION AND ACYLATION OF 3-HALOALKYL BETA-SULTAMS AND SYNTHESIS OF BICYCLIC BETA-SULTAMS

Alkylation of the 3-chloroethyl substituted beta-sultam 1 with bromoacetates yields the N- and 3-substituted beta-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 beta-sultams 7, the analogous reaction of 9 failed. The bicyclic beta-sultams 12 and 14 are obtained from 3-hydroxyalkyl beta-sultams 11 and 13 and carbonyl compounds. None of the prepared beta-sultams showed any antibacterial activity.