Selective synthesis and structural elucidation of S-acyl- and N-acylcysteines.
N-(Acyl)-1H-benzotriazoles 6a-f react with l-cysteine 5 at 20 degrees C to give exclusively (i) N-acyl-l-cysteines 8a-e in the presence of triethylamine in CH(3)CN-H(2)O (3:1), but (ii) S-acyl-l-cysteines 7a-e in CH(3)CN-H(2)O (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 (1)H-(15)N CIGAR-gHMBC experiments. The structure of compound 8d was also supported by single-crystal X-ray diffraction.
Katritzky
Alan R
AR
Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, Florida 32611-7200, USA. katritzky@chem.ufl.edu
Tala
Srinivasa R
SR
Abo-Dya
Nader E
NE
Gyanda
Kapil
K
El-Gendy
Bahaa El-Dien M
Bel-D
Abdel-Samii
Zakaria K
ZK
Steel
Peter J
PJ
D000097:Acetonitriles / Q000737:chemistry; D000215:Acylation; D003545:Cysteine / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry; D005021:Ethylamines / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D009584:Nitrogen / Q000737:chemistry*; D013455:Sulfur / Q000737:chemistry*; D014230:Triazoles / Q000737:chemistry; D014867:Water / Q000737:chemistry; D014961:X-Ray Diffraction
D000097:Acetonitriles; D005021:Ethylamines; D014230:Triazoles; D014867:Water; D013455:Sulfur; D003545:Cysteine; D009584:Nitrogen; C016162:triethylamine