Iridium-Catalyzed Direct Cyclization of Aromatic Amines with Diols

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  • Maki Minakawa
    Department of Applied Chemistry, Chemical Engineering and Biochemical Engineering, Yamagata University
  • Kouichi Watanabe
    Department of Chemistry, College of Humanities & Science, Nihon University
  • Satoru Toyoda
    Department of Applied Chemistry, Chemical Engineering and Biochemical Engineering, Yamagata University
  • Yasuhiro Uozumi
    Institute for Molecular Science

抄録

<jats:p>We developed an environmentally friendly iridium-catalyzed direct cyclization of aromatic amines with diols that generates the corresponding N-heterocyclic compounds with water as the sole by-product. Thus, under conditions of 165 °C for 18 hours, the direct cyclization of N-methylanilines with 1,3-propanediol by using an IrCl3 catalyst with rac-BINAP as a ligand in mesitylene afforded the corresponding tetrahydroquinoline derivatives with yields ranging from 73 to 83%. ­Under similar reaction conditions, direct cyclization of anilines with 1,3-propanediol produced the corresponding tetrahydrobenzoquinolizine derivatives with yields ranging from 26 to 76%.</jats:p>

収録刊行物

  • Synlett

    Synlett 29 (18), 2385-2389, 2018-10-02

    Georg Thieme Verlag KG

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