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Molecules. 2020 Jan 16;25(2). pii: E376. doi: 10.3390/molecules25020376.

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.

Author information

1
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.

Abstract

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.

KEYWORDS:

2-pyridineselenenyl halides; 2-pyridinesulfenyl halides; [1,3]selenazolo[3,2-a]pyridin-4-ium derivatives; [1,3]thiazolo[3,2-a]pyridin-4-ium derivatives; anethole; eugenol; isoeugenol

PMID:
31963275
DOI:
10.3390/molecules25020376
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