Staff Members - Benha University
Selective Synthesis and Structural Elucidation of S-Acyl- and N-Acylcysteines
• 2009
Publication Information
Authors
Alan R. Katritzky, Srinivasa R. Tala, Nader E. Abo-Dya, Kapil Gyanda, Bahaa El-Dien M. El-Gendy, Zakaria K. Abdel-Samii and Peter J. Steel
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publication.type
International
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Abstract
N-(Acyl)-1H-benzotriazoles 6a−f react with l-cysteine 5 at 20 °C to give exclusively (i) N-acyl-l-cysteines 8a−e in the presence of triethylamine in CH3CN−H2O (3:1), but (ii) S-acyl-l-cysteines 7a−e in CH3CN−H2O (5:1) in the absence of base. Structures 7b, 7d and 8b, 8d are supported by 2D NMR spectroscopic methods including gDQCOSY, gHMQC, gHMBC, and 1H−15N CIGAR-gHMBC experiments. The structure of compound 8d was also supported by single-crystal X-ray diffraction.