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MULTICOMPONENT SYNTHESIS AND BIOLOGICAL ACTIVITY OF (SULFANYLALKYL)-SUBSTITUTED AZAHETEROCYCLES

В. Р. Ахметова, Н. С. Ахмадиев, Е. С. Мещерякова, Л. М. Халилов, А. Г. Ибрагимов
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Abstract


A multicomponent reaction of acetylacetone with formaldehyde and S-nucleophiles (Н2S, 1,2‑ethanedithiol) in the presence of Lewis acids, followed by in situ interaction with hydrazine or hydroxylamine enabled a one-pot synthesis of 4,4'-[methane(ethane-1,2)diylbis(sulfanediylmethanediyl)]-bis(3,5-dimethyl-1H-pyrazoles) and 4,4'-[ethane-1,2-diylbis(sulfanediylmethanediyl)]bis(3,5-dimethyl-isoxazole). A one-pot synthesis of dithiane and dithiepane derivatives functionalized with oxo groups was performed by reacting malonic ester with formaldehyde and S-nucleophiles (Н2S, 1,2-ethanedithiol) in the presence of Lewis acids. Several of the obtained compounds exhibit fungicidal activity against fungal pathogens of plants.

How to Cite
Akhmetova, V. R.; Akhmadiev, N. S.; Meshcheryakova, E. S.; Khalilov, L. M.; Ibragimov, A. G. Chem. Heterocycl. Compd. 2014, 50, 742. [Khim. Geterotsikl. Soedin. 2014, 806.]

For this article in the English edition see DOI 10.1007/s10593-014-1529-9


Keywords


azaheterocycles; 1,3-dicarbonyl compounds; Lewis acids; N,S-nucleophiles; biological activity; catalysis; multicomponent reaction; X-ray structural analysis

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