Synthesis of 1,2,5‐Oxadiazinane Derivatives by Photochemical Cycloaddition of Nitrones with Diaminomethanes

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  • Kennosuke Itoh
    Laboratory of Medicinal Chemistry, School of Pharmacy Kitasato University Tokyo 108-8641 Japan
  • Atsushi Takashino
    Laboratory of Medicinal Chemistry, School of Pharmacy Kitasato University Tokyo 108-8641 Japan
  • Atsushi Ohtsuka
    Department of Chemistry, Graduate School of Science Kitasato University Kanagawa 252-0373 Japan
  • Mizuki Kobe
    Department of Chemistry, Graduate School of Science Kitasato University Kanagawa 252-0373 Japan
  • Shunsuke Sawamura
    Laboratory of Medicinal Chemistry, School of Pharmacy Kitasato University Tokyo 108-8641 Japan
  • Ryo Kato
    Department of Materials Chemistry, Faculty of Engineering Shinshu University Nagano 380-8553 Japan
  • Shigeto Hirayama
    Laboratory of Medicinal Chemistry, School of Pharmacy Kitasato University Tokyo 108-8641 Japan
  • Fumika Karaki
    Laboratory of Medicinal Chemistry, School of Pharmacy Kitasato University Tokyo 108-8641 Japan
  • Takaaki Mizuguchi
    Laboratory of Medicinal Chemistry, School of Pharmacy Kitasato University Tokyo 108-8641 Japan
  • Noriko Sato
    Medicinal Research Laboratories, School of Pharmacy Kitasato University Tokyo 108-8641 Japan
  • Ken Tokunaga
    Division of Liberal Arts Center for Promotion of Higher Education Kogakuin University Tokyo 192-0015 Japan
  • Yasunori Toda
    Department of Materials Chemistry, Faculty of Engineering Shinshu University Nagano 380-8553 Japan
  • Hiroyuki Suga
    Department of Materials Chemistry, Faculty of Engineering Shinshu University Nagano 380-8553 Japan
  • Hitoshi Ishida
    Department of Chemistry, Graduate School of Science Kitasato University Kanagawa 252-0373 Japan
  • Hideaki Fujii
    Laboratory of Medicinal Chemistry, School of Pharmacy Kitasato University Tokyo 108-8641 Japan

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<jats:title>Abstract</jats:title><jats:p>1,2,5‐Oxadiazinanes have a unique heterocyclic skeleton and are expected to be applicable to the synthesis of drugs. However, there have been few reported methodologies to synthesize these structures. We report a facile synthesis of 1,2,5‐oxadiazinanes that is accomplished by the unprecedented photochemical cycloaddition reaction of nitrones with diaminomethanes. The photoreaction is a formal [3+3] cycloaddition, where a nitrone and a diaminomethane act as the 1,3‐dipole and the 1,3‐synthon, respectively. The reaction is significantly accelerated with benzophenone as a photosensitizer. A high degree of diastereoselective addition (<jats:italic>d.r</jats:italic>. >99 : 1) is observed in the reaction of (<jats:italic>Z</jats:italic>)‐<jats:italic>N</jats:italic>‐benzyl‐1‐phenylmethanimine oxide with di(pyrrolidin‐1‐yl)methane.</jats:p>

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