Substituted 1,2-Thiazetidine 1,1-Dioxides. Synthesis and Properties of N-Alkylated and N-Acylated Derivatives of 1,2-Thiazetidine-3-acetic Acid 1,1-Dioxide

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1,2-Thiazetidine-3-acetic acid 1,1-dioxide was N-alkylated using bromoacetates, and N-acylated using either acyl chlorides, protected amino acid fluorides, or N-protected amino acid NCA, which seemed to be the most universal method. Most of the obtained “β-sultam peptides” were sensitive against humidity, they hydrolyzed forming sulfonic acids, and reactions with amines resulted in sulfonamides. Reactions of N-acylated products showed that the sulfonyl group was faster attacked than the imide structure.

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Correspondence to Hans-Hartwig Otto.

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Röhrich, T., Thaher, B. & Otto, H. Substituted 1,2-Thiazetidine 1,1-Dioxides. Synthesis and Properties of N-Alkylated and N-Acylated Derivatives of 1,2-Thiazetidine-3-acetic Acid 1,1-Dioxide. Monatshefte für Chemie 135, 55–68 (2004). https://doi.org/10.1007/s00706-003-0105-2

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  • Keywords. 1,2-Thiazetidine 1,1-dioxide; β-Sultam; β-Sultam peptide.