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

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概要

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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 (δ0.13-0.82ppm) 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.

• 2007-10-01

著者

• Suga Hiroyuki

  岡山大学 医歯総研究 麻酔蘇生学

• Suga Hiroyuki

  Department Of Cardiovascular Dynamics National Cardiovascular Center Research Institute

• Suga H

  Department Of Physiology Ii Okayama University Medical School

• Kakehi A

  Department Of Chemistry And Material Engineering Faculty Of Engineering Shinshu University

• Suga Hiroyuki

  Department Of Systems Physiology Okayama University Graduate School Of Medicine Dentistry And Pharma

• KAKEHI Akikazu

  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

• Akikazu Kakehi

  Department Of Chemistry And Material Engineering Faculty Of Engineering Shinshu University

• Kakehi Akikazu

  Department Of Chemistry And Material Engineering Faculty Of Engineering Shinshu University

• Suga H

  Department Of Systems Physiology Okayama University Graduate School Of Medicine Dentistry And Pharma

• Suga Hiroyuki

  Department Of Chemistry And Material Engineering Faculty Of Engineering Shinshu University

• Kakehi A

  Dep. Of Chemistry And Material Engineering Fac. Of Engineering Shinshu Univ. Wakasato Nagano 380-855

• Ohta A

  Mitsubishi Electric Corp. Itami‐shi Jpn

• Suga H

  Dep. Of Chemistry And Material Engineering Fac. Of Engineering Shinshu Univ. Wakasato Nagano 380-855

• Ohta A

  Faculty Of Science 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

• Suga Hiroyuki

  Dep. Of Chemistry And Material Engineering Fac. Of Engineering Shinshu Univ. Wakasato Nagano 380-855

• SUGA Hiroyuki

  Department of Cardiac Physiology, National Cardiovascular Center Research Institute

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