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

Abstract

Abstract 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.