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

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Chemistry of Heterocyclic Compounds Aims and scope

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.

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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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Authors and Affiliations

  1. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky St, Irkutsk, 664033, Russia

    Ekaterina А. Grebneva, Yuliya I. Bolgova, Olga M. Trofimova, Aleksander I. Albanov & Tat’yana N. Borodina

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  1. Ekaterina А. Grebneva
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  2. Yuliya I. Bolgova
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  3. Olga M. Trofimova
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  4. Aleksander I. Albanov
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  5. Tat’yana N. Borodina
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Correspondence to Olga M. Trofimova.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2019, 55(8), 762–767

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Grebneva, E.А., Bolgova, Y.I., Trofimova, O.M. et al. Synthesis and structure of novel Si-substituted silylpropyl derivatives of 2-mercaptobenzoxazole and 2-mercaptobenzothiazole. Chem Heterocycl Comp 55, 762–767 (2019). https://doi.org/10.1007/s10593-019-02532-3

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  • DOI: https://doi.org/10.1007/s10593-019-02532-3

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