Preparation of New Nitrogen-Bridged Heterocycles. 55. Reinvestigation of the Bromination/Dehydrobromination of Ethyl 3-[2-(Methylthio)indolizin-3-yl]acrylate Derivatives

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  • Kakehi Akikazu
    Department of Chemistry and Material Engineering, Faculty of Engineering, Shinshu University
  • Ito Suketaka
    Department of Chemistry and Material Engineering, Faculty of Engineering, Shinshu University
  • Suga Hiroyuki
    Department of Chemistry and Material Engineering, Faculty of Engineering, Shinshu University
  • Kobayashi Yuhichi
    Department of Chemistry and Material Engineering, Faculty of Engineering, Shinshu University
  • Zuo Peng
    Department of Chemistry and Material Engineering, Faculty of Engineering, Shinshu University
  • Iriye Ryozo
    Department of Bioscience and Biotechnology, Faculty of Agriculture, Shinshu University

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The bromination/dehydrobromination reactions of ethyl 3-[1-alkoxycarbonyl-2-(methylthio)indolizin-3-yl]acrylates were reinvestigated. Reactions of the title compounds with two equivalents of bromine, followed by heating of the resulting reaction mixture and then treatment with a base gave the unexpected dialkyl 7-bromothieno[2,3-b]indolizine-2,9-dicarboxylates, while similar reactions using benzyltrimethylammonium tribromide as a brominating agent afforded only non-brominated thieno[2,3-b]indolizine derivatives, which were converted to the corresponding 7-bromo derivatives upon further treatment with bromine.

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