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.
Highlights
Sulfur-containing rings condensed with nitrogen heterocycles are important scaffolds for medicinal chemistry [1]
We increased the yield of compound annulation reactions withletter
We studied the2 reactions of 2-pyridinesulfenyl and 2-pyridineselenenyl bromides with a series
Summary
Sulfur-containing rings condensed with nitrogen heterocycles are important scaffolds for medicinal chemistry [1]. Condensed sulfur/nitrogen heterocycles have always been a vital part of new drug discovery. Penicillin and cephalosporin antibiotics contain sulfur-containing ring condensed with a nitrogen heterocycle as the key scaffold [1]. Thiazole ring presents in many natural and biologically active compounds including ritonavir (anti-HIV), sulfathiazole (antimicrobial), and tiazofurin (anticancer) drugs [1,2,3]. The combination of the thiazole ring with the pyridine heterocycle in one condensed molecule gives a very promising scaffold for medicinal chemistry. The thiazolopyridine derivatives are associated with a wide range of pharmacological activities
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