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Properties and Reactions of Substituted 1,2‐Thiazetidine 1,1‐Dioxides: Reactions of 3‐Acetoxy‐β‐sultams with Sulfur Nucleophiles
Author(s) -
Merkle Stefan,
Otto HansHartwig
Publication year - 1994
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.19943271011
Subject(s) - nucleophile , chemistry , moiety , electrophile , sulfur , silylation , organic chemistry , medicinal chemistry , catalysis
The acetate moiety of 3‐acetoxy‐β‐sultams 2 is easily displaced by sulfur nucleophiles yielding the alkylthio‐β‐sultams 3 which are transformed into stable derivatives 4 by silylation. The synthesis of the cephem analogue 7 is described. Reactions of 2 with thiols under electrophilic conditions result in the formation of bis‐substituted ethanesulfonamides 6 and 9 .