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Preparation of sulfonamides from N-silylamines.

ABSTRACT: Sulfonamides have been prepared in high yields by the reactions of N-silylamines with sulfonyl chlorides and fluorides. In a competition experiment, the sulfonyl chlorides were found to be far more reactive than sulfonyl fluorides. The chemistry may be used to prepare aliphatic, aromatic, tertiary, secondary, and primary sulfonamides. It may also be done in the absence of solvent and the byproduct trimethylsilyl chloride recovered in good yield. Primary sulfonamides were synthesized from the sulfonyl chloride with aminotriphenyl silane (Ph₃SiNH₂), a conversion demonstrated with the synthesis of the carbonic anhydrase inhibitor, acetazolamide.

SUBMITTER: Naredla RR

PROVIDER: S-EPMC5333644 | biostudies-literature | 2013 Nov

REPOSITORIES: biostudies-literature

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Preparation of sulfonamides from N-silylamines.

Naredla Rajasekhar Reddy RR Klumpp Douglas A DA

Tetrahedron letters 20131101 45

Sulfonamides have been prepared in high yields by the reactions of N-silylamines with sulfonyl chlorides and fluorides. In a competition experiment, the sulfonyl chlorides were found to be far more reactive than sulfonyl fluorides. The chemistry may be used to prepare aliphatic, aromatic, tertiary, secondary, and primary sulfonamides. It may also be done in the absence of solvent and the byproduct trimethylsilyl chloride recovered in good yield. Primary sulfonamides were synthesized from ...[more]

PMID: 28260818

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