Novel Synthetic Methods of Eight- and Nine-Membered Cyclic Amine Derivatives Based on Friedel-Crafts Reaction via Iminium Ion

DOI

Bibliographic Information

Other Title
  • イミニウムイオンのFriedel-Crafts環化による含窒素８、９員環の合成

Description

The Pictet-Spengler reaction is one of the most useful methods for synthesizing tetrahydroisoquinoline. This reaction is a kind of Friedel-Crafts reaction. We found that an intramolecular Friedel-Crafts reaction of the iminium cation afforded eight- and nine-membered cyclic amines fused with a benzene ring in high yield. Treatment of sulfonamide derivatives with an aromatic ring possessing one or two methyl groups with TMSOTf gave 1,2,3,4,5,6-hexahydrobenzo[c]azocine derivatives in high yields. Moreover, when sulfonamide derivatives having an acetylene cobalt complex moiety were subjected to the same conditions, not only eight-membered cyclic amine but also nine-membered cyclic amine was obtained in high yield.

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Details 詳細情報について

  • CRID
    1390282680610544512
  • NII Article ID
    130006995986
  • DOI
    10.14895/hannou.32.0.38.0
  • Text Lang
    ja
  • Data Source
    • JaLC
    • CiNii Articles
  • Abstract License Flag
    Disallowed

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