Preparation of New Nitrogen-Bridged Heterocycles. 60. Syntheses and Conformational Analyses of Bis(indolizin-1-yl) Disulfides

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  • Kakehi Akikazu
    Department of Chemistry and Material Engineering, Faculty of Engineering, Shinshu University
  • Suga Hiroyuki
    Department of Chemistry and Material Engineering, Faculty of Engineering, Shinshu University
  • Okuno Hiroko
    Department of Chemistry and Material Engineering, Faculty of Engineering, Shinshu University
  • Okuhara Masaki
    Department of Chemistry and Material Engineering, Faculty of Engineering, Shinshu University
  • Ohta Akira
    Faculty of Science, Shinshu University

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Some bis(indolizin-1-yl) disulfides, readily obtainable from the treatment of 1-(benzoylthio)indolizines with piperidine, were prepared and their conformations were investigated. In comparison with those of 1-(benzoylthio)indolizines, the 1H-NMR spectra of these disulfides showed considerable high field shifts (δ 0.13—0.82 ppm) on each pyridine ring proton and the UV spectra exhibited significant bathochromic and hyperchromic shifts. These results supported strongly the participation of an intramolecular π–π interaction between the two indolizine rings in these molecules and, hence, of a particular gauche (cis) conformation. However, the conformational considerations and molecular calculations (Mopac PM3) for some bis(indolizin-1-yl) disulfides showed the presence of four more stable gauche forms in which two are enantiomeric, resulting in three types of gauche structures. These three types of gauche structures were confirmed by X-ray analyses.

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