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Chemistry of Heterocyclic Compounds

, Volume 55, Issue 9, pp 823–826 | Cite as

Dioxothietanylation of heterocycles 2*. Imidazoles and benzimidazoles

  • Nadezhda N. MakarovaEmail author
  • Elena E. Klen
  • Ferkat А. Khaliullin
Article
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1-(1,1-Dioxidothietan-3-yl)-1H-imidazoles and 1-(1,1-dioxidothietan-3-yl)-1H-benzimidazoles were synthesized in the reaction of 3,5-dibromo-1-(1,1-dioxidothietan-3-yl)-1H-1,2,4-triazole with the sodium salts of imidazoles and benzimidazoles. The reaction involves addition of azoles to thiete 1,1-dioxide formed in situ, which acts as a Michael acceptor. The effect of pKa values of imidazoles and benzimidazoles on their reactivity is shown.

Keywords

benzimidazole imidazole thietane 1,1-dioxide 1,2,4-triazole aza-Michael reaction dioxothietanylation 

Notes

Supplementary material

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Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2019

Authors and Affiliations

  • Nadezhda N. Makarova
    • 1
    Email author
  • Elena E. Klen
    • 1
  • Ferkat А. Khaliullin
    • 1
  1. 1.Bashkir State Medical UniversityUfaRussia

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