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Chemistry of Heterocyclic Compounds

, Volume 55, Issue 8, pp 762–767 | Cite as

Synthesis and structure of novel Si-substituted silylpropyl derivatives of 2-mercaptobenzoxazole and 2-mercaptobenzothiazole

  • Ekaterina А. Grebneva
  • Yuliya I. Bolgova
  • Olga M. TrofimovaEmail author
  • Aleksander I. Albanov
  • Tat’yana N. Borodina
Article
  • 12 Downloads

A previously unknown carbofunctional (trimethoxysilyl)propyl derivative of the 2-mercaptobenzoxazole, C6H4NOCS(CH2)3Si(OMe)3, containing a tetracoordinated silicon atom was synthesized by nucleophilic substitution of the chlorine atom in the (3-chloropropyl)-trimethoxysilane with the benzoxazol-2-ylsulfanyl group. The reaction of 2-[(trimethoxysilyl)propylsulfanyl]benzoxazole or –benzothiazole with boron trifluoride etherate led to a previously unknown hydrolytically unstable Si-fluoropropyl derivatives of 2-mercaptobenzoxazole or 2-mercaptobenzothiazole, C6H4N(Y)CS(CH2)3SiF3 (Y = O, S). By transesterification of 2-[(trimethoxysilyl)-propylsulfanyl]benzoxazole by tris(2-hydroxyethyl)amine, a new silatranylpropyl derivative of 2-mercaptobenzoxazole containing an intramolecular coordination bond N→Si and a pentacoordinated silicon atom, C6H4NOCS(CH2)3Si(OCH2CH2)3N, was obtained.

Keywords

(3-chloropropyl)trimethoxysilane 2-mercaptobenzoxazole 2-mercaptobenzotriazole silatrane trifluorosilane 

Notes

The main results were obtained using the material and technical base of the Baikal Analytical Center for Collective Use of the Siberian Branch of the Russian Academy of Sciences.

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Copyright information

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

Authors and Affiliations

  • Ekaterina А. Grebneva
    • 1
  • Yuliya I. Bolgova
    • 1
  • Olga M. Trofimova
    • 1
    Email author
  • Aleksander I. Albanov
    • 1
  • Tat’yana N. Borodina
    • 1
  1. 1.Favorsky Irkutsk Institute of ChemistrySiberian Branch of the Russian Academy of SciencesIrkutskRussia

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