| publication name | Selective Synthesis and Structural Elucidation of S-Acyl- and N-Acylcysteines |
|---|---|
| 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 |
| year | 2009 |
| keywords | |
| journal | |
| volume | Not Available |
| issue | Not Available |
| pages | Not Available |
| publisher | Not Available |
| Local/International | International |
| Paper Link | http://pubs.acs.org/doi/abs/10.1021/jo900853s |
| Full paper | download |
| Supplementary materials | Not Available |
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.