Properties and Reactions of Substituted 1,2‐Thiazetidine 1,1‐Dioxides: Reactions of 3‐Acetoxy‐β‐sultams with Sulfur Nucleophiles | Zendy

Merkle Stefan | Zendy; Otto HansHartwig | Zendy

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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 .

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