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 bromoac etates yields the N- and 3-substituted beta-sultams 2; exchange of hal ogens affords esters 3. Reactions of 1 or of the analogues 8 with isoc yanates make the carbamoyl derivatives 5, 6, and 9 available. While cy clization 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 an d 13 and carbonyl compounds. None of the prepared beta-sultams showed any antibacterial activity.