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

Authors

  • В. Р. Ахметова Institute of Petrochemistry and Catalysis, Russian Academy of Sciences
  • Н. С. Ахмадиев Institute of Petrochemistry and Catalysis, Russian Academy of Sciences
  • Е. С. Мещерякова Institute of Petrochemistry and Catalysis, Russian Academy of Sciences
  • Л. М. Халилов Institute of Petrochemistry and Catalysis, Russian Academy of Sciences
  • А. Г. Ибрагимов Institute of Petrochemistry and Catalysis, Russian Academy of Sciences

DOI:

https://doi.org/10.1007/1603

Keywords:

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

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

Author Biographies

В. Р. Ахметова, Institute of Petrochemistry and Catalysis, Russian Academy of Sciences

Внира Рахимовна Ахметова

Лаборатория гетероатомных соединений, д.х.н., профессор

Н. С. Ахмадиев, Institute of Petrochemistry and Catalysis, Russian Academy of Sciences

Наиль Салаватович Ахмадиев

Лаборатория гетероатомных соединений, стажер исследователь

Е. С. Мещерякова, Institute of Petrochemistry and Catalysis, Russian Academy of Sciences

Екатерина Сергеевна Мещерякова

Лаборатория структурной химии, аспирант

Л. М. Халилов, Institute of Petrochemistry and Catalysis, Russian Academy of Sciences

Леонард Мухибович Халилов

Заведующий лабораторией структурной химии, д.х.н., профессор

А. Г. Ибрагимов, Institute of Petrochemistry and Catalysis, Russian Academy of Sciences

Асхат Габдрахманович Ибрагимов

Заведующий лабораторией гетероатомных соединений, д.х.н., профессор

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Published

2014-06-01

Issue

No. 5 (2014)

Section

Original Papers