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Open AccessFeature PaperArticle

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

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A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Division of The Russian Academy of Sciences, 1 Favorsky Str., Irkutsk 664033, Russian
2
Pedagogical Institute, Irkutsk State University, 6 Nizhniaja Naberezhnaya Str., Irkutsk 664003, Russia
*
Author to whom correspondence should be addressed.
Academic Editor: Oleg A. Rakitin
Molecules 2020, 25(2), 376; https://doi.org/10.3390/molecules25020376
Received: 2 December 2019 / Revised: 5 January 2020 / Accepted: 13 January 2020 / Published: 16 January 2020
(This article belongs to the Special Issue Polysulfur- and Sulfur-Nitrogen Heterocycles)
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 2H,3H-[1,3]thia- and -selenazolo[3,2-a]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. View Full-Text
Keywords: anethole; eugenol; isoeugenol; 2-pyridinesulfenyl halides; 2-pyridineselenenyl halides; [1,3]thiazolo[3,2-a]pyridin-4-ium derivatives; [1,3]selenazolo[3,2-a]pyridin-4-ium derivatives anethole; eugenol; isoeugenol; 2-pyridinesulfenyl halides; 2-pyridineselenenyl halides; [1,3]thiazolo[3,2-a]pyridin-4-ium derivatives; [1,3]selenazolo[3,2-a]pyridin-4-ium derivatives
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MDPI and ACS Style

Potapov, V.A.; Ishigeev, R.S.; Shkurchenko, I.V.; Zinchenko, S.V.; Amosova, S.V. Natural Compounds and Their Structural Analogs in Regio- and Stereoselective Synthesis of New Families of Water-Soluble 2H,3H-[1,3]thia- and -Selenazolo[3,2-a]pyridin-4-ium Heterocycles by Annulation Reactions. Molecules 2020, 25, 376.

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