Enantiomeric Separation of New Chiral Azole Compounds

Twelve new azole compounds were synthesized through an ene reaction involving methylidene heterocycles and phenylmaleimide, producing four oxazoles, five thiazoles, and one pyridine derivative, and ethyl glyoxal for an oxazole and a thiazole compound. The twelve azoles have a stereogenic center in t...

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Bibliographic Details
Published in:Molecules (Basel, Switzerland) Switzerland), 2021-01, Vol.26 (1), p.213
Main Authors: Kenari, Marziyeh E, Putman, Joshua I, Singh, Ravi P, Fulton, Brandon B, Phan, Huy, Haimour, Reem K, Tse, Key, Berthod, Alain, Lovely, Carl J, Armstrong, Daniel W
Format: Article
Language:English
Subjects:
Alcohol
Amylose
Amylose - chemistry
Analytical chemistry
Antibiotics
Azoles
Azoles - chemistry
Azoles - isolation & purification
Carbohydrates
Carbon
Chemical Sciences
Chromatography
Elution
enantiomer separation
Enantiomers
Glycopeptides
Glycopeptides - chemistry
Heterocyclic compounds
macrocyclic glycopeptides
Maltodextrin
mobile phase modes
Molecular Structure
Oxazole
Polysaccharides - chemistry
pyridine
Pyridines
Selectors
Stationary phase
Stereoisomerism
thiazole
Thiazoles
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Summary:Twelve new azole compounds were synthesized through an ene reaction involving methylidene heterocycles and phenylmaleimide, producing four oxazoles, five thiazoles, and one pyridine derivative, and ethyl glyoxal for an oxazole and a thiazole compound. The twelve azoles have a stereogenic center in their structure. Hence, a method to separate the enantiomeric pairs, must be provided if any further study of chemical and pharmacological importance of these compounds is to be accomplished. Six chiral stationary phases were assayed: four were based on macrocyclic glycopeptide selectors and two on linear carbohydrates, i.e., derivatized maltodextrin and amylose. The enantiomers of the entire set of new chiral azole compounds were separated using the three different mobile phase elution modes: normal phase, polar organic, and reversed phase. The most effective chiral stationary phase was the MaltoShell column, which was able to separate ten of the twelve compounds in one elution mode or another. Structural similarities in the newly synthesized oxazoles provided some insights into possible chiral recognition mechanisms.
ISSN:1420-3049
1420-3049
DOI:10.3390/MOLECULES26010213