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Enantiodifferentiation of Thiohydantoin Derivatives by NMR in the Presence of Chiral Solvating Agent: (1R,2S)-Ephedrine and Chiral Symmetrical and Unsymmetrical Thioureas.
Chirality
February 2025
Department of Chemistry, Bogazici University, Istanbul, Turkey.
2-Thiohydantoin derivatives, including different substitutions at N-1 and C-5 (5-methyl-, 5-isopropyl-, 1-acetyl-5-methyl-, and 1-acetyl-5-isopropyl-) (1-4, respectively), were synthesized by the known literature methods. In these synthetic pathways, it was reported that enantiomerically pure 2-thiohydantions were obtained in the absence of any solvent via the reaction of L-amino acids with thiourea (1&2) and via the reaction of L-amino acids with NHSCN and acetic anhydride (3&4). However, in this study, in contrary to the previous literature studies, racemic mixtures of 2-thiohydantoins were obtained although the same synthetic methods were used.
View Article and Find Full Text PDFThe Reduction of Carbonyl Compounds with Dicyclopentylzinc: A New Example of Asymmetric Amplifying Autocatalysis.
Int J Mol Sci
December 2023
N. D. Zelinsky Institute of Organic Chemistry, Leninsky Prosp. 47, 119991 Moscow, Russia.
A previously unknown reduction of carbonyl compounds with dicyclopentylzinc is reported. Aldehydes react in mild conditions yielding corresponding primary alcohols and cyclopentene. Although cyclohexanone and acetophenone are inert to dicyclopentylzinc, a variety of heterocyclic ketones reacted readily, yielding reasonable to high yields of corresponding secondary alcohols.
View Article and Find Full Text PDFIdentification and characterization of chemically masked derivatives of pseudoephedrine, ephedrine, methamphetamine, and MDMA.
Drug Test Anal
April 2020
School of Chemical Sciences, University of Auckland, Auckland, New Zealand.
The emergence of chemically masked illicit drugs represents a challenge to global initiatives that are working to prevent their manufacture and distribution. Targeted analytical techniques currently used by law enforcement to identify unknown materials rely on spectroscopic and spectrophotometric databases that do not currently include some of these compounds, making their identification challenging. This study aimed to update compound spectral libraries to aid in the rapid detection and identification of these masked drugs, as well as to provide insight into their synthetic procedures.
View Article and Find Full Text PDFCrystal structures and other properties of ephedrone (methcathinone) hydrochloride, -acetylephedrine and -acetylephedrone.
Forensic Toxicol
August 2018
3Center for Translational Research and Molecular Biology of Cancer, Maria Skłodowska-Curie Memorial Cancer Centre and Institute of Oncology, 44-100 Gliwice, Poland.
Purpose: Three compounds obtained from ephedrine were identified and characterized by various instrumental analytical methods. Ephedrone (methcathinone) hydrochloride and its fundamental derivatives -acetylephedrine and -acetylephedrone were analyzed as precursors of a cathinone derivative.
Methods: The obtained samples were analyzed by gas chromatography coupled with mass spectrometry, nuclear magnetic resonance spectroscopy, infrared and Raman spectroscopy, and X-ray crystallography.
Separation of enantiomers of ephedrine by capillary electrophoresis using cyclodextrins as chiral selectors: comparative CE, NMR and high resolution MS studies.
Electrophoresis
October 2011
Department of Analytical Chemistry, Faculty of Chemistry, University of Alcalá, Alcalá de Henares, Madrid, Spain.
The enantiomer migration order (EMO) of ephedrine was investigated in the presence of various CDs in CE. The molecular mechanisms of chiral recognition were followed for the ephedrine complexes with native α- and β-CD and heptakis(2,3-di-O-acetyl-6-O-sulfo)-β-CD (HDAS-β-CD) by CE, NMR spectroscopy and high-resolution MS. Minor structural differences were observed between the complexes of ephedrine with α- and β-CD although the migration order of enantiomers was opposite when these two CDs were applied as chiral selectors in CE.
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