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Synthesis and Transformations of 2,4,4,7-Tetramethyl-4-silanaphtho[3,2-b]thiophen-9-one

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Abstract

The catalytic dehydrocyclization of dimethyl(5-methyl-2-thienyl)(2,4-dimethylphenyl)silane accompanied by a skeletal rearrangement gives 2,4,4,7-tetramethyl-4,9-dihydro-4-silanaphtho[3,2-b]thiophene, which was oxidized to 2,4,4,7-tetramethyl-4-silanaphtho[3,2-b]thiophen-9-one, whose structure was solved by X-ray diffraction structural analysis. Various chemical transformations of the ketone synthesized were performed including radical bromination by bromosuccinimide, condensation with furfural in the presence of KOH, reduction by LiAlH4, and nitration by acetyl nitrate.

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Authors and Affiliations

  1. IREA Federal State Unitary Firm, Moscow, 107076, Russia

    V. M. Polosin & A. A. Astakhov

  2. Russian Academy of Sciences, N. D. Zelinsky Institute of Organic Chemistry, Moscow, 119991, Russia

    M. A. Ryashentseva

Authors
  1. V. M. Polosin
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  2. A. A. Astakhov
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  3. M. A. Ryashentseva
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Polosin, V.M., Astakhov, A.A. & Ryashentseva, M.A. Synthesis and Transformations of 2,4,4,7-Tetramethyl-4-silanaphtho[3,2-b]thiophen-9-one. Chemistry of Heterocyclic Compounds 39, 1249–1254 (2003). https://doi.org/10.1023/B:COHC.0000008275.26329.56

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  • DOI: https://doi.org/10.1023/B:COHC.0000008275.26329.56

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