SYNTHESIS AND TRANSFORMATIONS OF 2,4,4,7-TETRAMETHYL-4-SILA-NAPHTHO[3,2-<i>b</i>]THIOPHEN-9-ONE

Authors

  • В. М. Полосин IREA Federal State Unitary Firm, Moscow 107076
  • А. А. Астахов IREA Federal State Unitary Firm, Moscow 107076
  • М. А. Ряшенцева N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow 119991

Keywords:

aluminum–chromium catalyst, 2,4,4,7-tetramethyl-4-silanaphtho[3,2-b]thiophen-9-one, bromination, reduction, dehydrocyclization, condensation, nitration

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.

How to Cite
Polosin, V. M.; Astakhov, A. A.; Ryashentseva, M. A. Chem. Heterocycl. Compd. 2003, 39, 1249. [Khim. Geterotsikl. Soedin. 2003, 1420.]

For this article in the English edition, see DOI 10.1023/B:COHC.0000008275.26329.56

 

 

 

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Published

2003-09-25

Issue

No. 9 (2003)

Section

Original Papers