Natural Compounds and Their Structural Analogs in Regio- and Stereoselective Synthesis of New Families of Water-Soluble 2 H ,3 H -[1,3]thia- and -Selenazolo[3,2- a ]pyridin-4-ium Heterocycles by Annulation Reactions

It has been found that both eugenol and isoeugenol derivatives reacted with 2-pyridinesulfenyl and 2-pyridineselenenyl halides in a regioselective mode affording products with opposite regiochemistry. Synthesis of new families of 2 ,3 -[1,3]thia- and -selenazolo[3,2- ]pyridin-4-ium heterocycles has...

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Bibliographic Details
Published in:Molecules (Basel, Switzerland) Switzerland), 2020-01, Vol.25 (2)
Main Authors: Potapov, Vladimir A, Ishigeev, Roman S, Shkurchenko, Irina V, Zinchenko, Sergey V, Amosova, Svetlana V
Format: Article
Language:English
Subjects:
Biological Products - chemical synthesis
Biological Products - chemistry
Biological Products - pharmacology
Chemistry Techniques, Synthetic
Molecular Structure
Pyridines - chemical synthesis
Pyridines - chemistry
Pyridines - pharmacology
Solubility
Spectrum Analysis
Structure-Activity Relationship
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Summary:It has been found that both eugenol and isoeugenol derivatives reacted with 2-pyridinesulfenyl and 2-pyridineselenenyl halides in a regioselective mode affording products with opposite regiochemistry. Synthesis of new families of 2 ,3 -[1,3]thia- and -selenazolo[3,2- ]pyridin-4-ium heterocycles has been developed by annulation reactions of 2-pyridinechalcogenyl halides with natural compounds (eugenol, isoeugenol, methyl eugenol, methyl isoeugenol, acetyl eugenol, trans-anethole) and their structural analogs. The influence of the substrate structure and the nature of halogen on the product yields are studied. The 2-pyridinesulfenyl and 2-pyridineselenenyl chlorides are more efficient reagents compared to corresponding bromides. The obtained condensed heterocycles are novel water-soluble functionalized compounds with promising biological activity.
ISSN:1420-3049