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

被引：19

作者：

Potapov, Vladimir A. ^{[1
]}

Ishigeev, Roman S. ^{[1
]}

Shkurchenko, Irina V. ^{[1
,2
]}

Zinchenko, Sergey V. ^{[1
]}

Amosova, Svetlana V. ^{[1
]}

机构：

[1] Russian Acad Sci, Siberian Div, AE Favorsky Irkutsk Inst Chem, 1 Favorsky Str, Irkutsk 664033, Russia

[2] Irkutsk State Univ, Pedag Inst, 6 Nizhniaja Naberezhnaya Str, Irkutsk 664003, Russia

来源：

MOLECULES | 2020年 / 25卷 / 02期

基金：

俄罗斯科学基金会;

关键词：

anethole; eugenol; isoeugenol; 2-pyridinesulfenyl halides; 2-pyridineselenenyl halides; 1; 3]thiazolo[3; 2-a]pyridin-4-ium derivatives; 3]selenazolo[3; SELENIUM DICHLORIDE; CHEMISTRY; ORGANOSELENIUM; DERIVATIVES; THIIRANIUM; REACTIVITY; DIHALIDES; THIAZOLE; REAGENTS; ALKENES;

D O I：

10.3390/molecules25020376

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

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.

引用

页数：15

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