Regioselective N-Methylation of 6-Chloroindolo[3,2-c]quinolines and Their Amination Reactivity at the C-6 Position

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  • Wang Ning
    Division of Chemistry and Biotechnology, Graduate School of Natural Science and Technology, Okayama University
  • Imai Kento
    Division of Chemistry and Biotechnology, Graduate School of Natural Science and Technology, Okayama University
  • Pang Cui-Qing
    Division of Chemistry and Biotechnology, Graduate School of Natural Science and Technology, Okayama University
  • Wang Ming-qi
    Division of Chemistry and Biotechnology, Graduate School of Natural Science and Technology, Okayama University
  • Yonezawa Mizuho
    Division of Chemistry and Biotechnology, Graduate School of Natural Science and Technology, Okayama University
  • Zhang Yu
    Division of Chemistry and Biotechnology, Graduate School of Natural Science and Technology, Okayama University
  • Nokami Junzo
    Department of Applied Chemistry, Faculty of Engineering, Okayama University of Science
  • Inokuchi Tsutomu
    Division of Chemistry and Biotechnology, Graduate School of Natural Science and Technology, Okayama University

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  • Regioselective <i>N</i>-Methylation of 6-Chloroindolo[3,2-<i>c</i>]quinolines and Their Amination Reactivity at the C-6 Position

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The treatment of 6-chloroindolo[3,2-c]quinoline 6 with NaH–MeI led to methylation at N-11, forming 8, while the reaction of 6 with MeI with heating gave the corresponding 5-methylated quinolinium salt whose SNAr with water smoothly proceeded to form 5-methylindolo[3,2-c]quinolin-6-one 3b. The amination reactivity at the C-6 was assigned in the order of 6 > 11-methylated 8.

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