Structure and Reactions of γ-Thiocyanatoacetoacetanilide

Abstract

The structure of various tautomeric forms of 3-oxo-4-thiocyanato-N-phenylbutanamide (γ-thiocyanatoacetoacetanilide) has been studied in detail and their stability has been assessed using NMR spectroscopy, X-ray analysis, and quantum-chemical calculations. The reactions of this compound with some C- and N-nucleophiles have been investigated, and the structure and tautomerism of the products are discussed. Contrary to literature data, the azo coupling reaction of γ-thiocyanatoacetoacetanilide with aryldiazonium salts leads to (Z)-2-[2-arylhydrazinylidene]-3-oxo-4-thiocyanato-N-phenylbutanamides, whose structure has been confirmed by single crystal X-ray analysis. The synthesized compounds were tested for antimicrobial activity, and one of the products exhibited moderate activity against S. enterica and S. aureus.