ZnCl₂-Promoted Intramolecular Hetero-Diels-Alder Reaction of o-Alkynylphenylcarbodiimides for Synthesis of Dihydrodibenzo[b,g][1,8]naphthyridines

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  • Kutsumura Noriki
    International Institute for Integrative Sleep Medicine (WPI-IIIS), University of Tsukuba Department of Chemistry, Faculty of Science, Tokyo University of Science
  • Koyama Yasuaki
    Department of Chemistry, Faculty of Science, Tokyo University of Science
  • Tateno Kotaro
    Department of Chemistry, Faculty of Science, Tokyo University of Science
  • Yamamoto Naoshi
    International Institute for Integrative Sleep Medicine (WPI-IIIS), University of Tsukuba
  • Nagase Hiroshi
    International Institute for Integrative Sleep Medicine (WPI-IIIS), University of Tsukuba
  • Saito Takao
    Department of Chemistry, Faculty of Science, Tokyo University of Science

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  • ZnCl<sub>2</sub>-Promoted Intramolecular Hetero-Diels–Alder Reaction of <i>o</i>-Alkynylphenylcarbodiimides for Synthesis of Dihydrodibenzo[<i>b</i>,<i>g</i>][1,8]naphthyridines

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<p>The ZnCl2-promoted intramolecular hetero-Diels–Alder reaction of N-(ortho-propargylphenyl)-N′-arylcarbodiimides, in which the aryl-N=C moiety functioned as a 2-azabuta-1,3-diene, 4π component, has been achieved. By this method, very rare 5,12-dihydrodibenzo[b,g][1,8]naphthyridines and fully aromatized dibenzo[b,g][1,8]naphthyridines were successfully synthesized.</p>

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