Preparation of New Nitrogen-Bridged Heterocycles. 51. Syntheses and Structures of Compounds Having Two Indolizine Nuclei in a Molecule.

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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
  • SAKURAI Shinji
    Department of Chemistry and Material Engineering, Faculty of Engineering, Shinshu University
  • KOBAYASHI Tomoshige
    Faculty of Science, Shinshu University

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New compounds having two indolizine nuclei in a molecule were prepared in low to moderate yields from the reactions of potassium 2-indolizinethiolates with 1,ω-dihalides such as 1,2-diiodoethane, 1,3-dibromopropane, 1,4-dibromobutane, α,α'-dichloro-o-xylene, and α,α'-dichloro-p-xylene. Most of the products had the conformation in which the two indolizine rings in the molecule are as remote as possible, but only 1,2-bis[[(2-indolizinyl)thio]methyl]benzene derivatives, prepared from potassium 2-indolizinethiolates and α,α'-dichloro-o-xylene, showed a weak attractive interaction between the two indolizine nuclei in the X-ray analysis and the nuclear Overhauser and exchange spectroscopy (NOESY) spectrum.

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