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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
Author(s) -
Schwenkkraus Peter,
Otto HansHartwig
Publication year - 1993
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.19933260802
Subject(s) - bicyclic molecule , chemistry , alkylation , acylation , halogen , medicinal chemistry , organic chemistry , catalysis , alkyl
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.