N-メチル化アミドのシス型優先性と芳香族分子構築  [in Japanese] Aromatic Architecture Based on cis Conformational Preference of N-Methylated Amides  [in Japanese]

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Abstract

Aromatic secondary amides such as benzanilide (1) exist in trans-amide form both in the crystal and in solution, whereas <I>N</I>-methylbenzanilide (2) exists in <I>cis</I> form in the crystal, and predominantly in <I>cis</I> form in various solutions. Similar <I>cis</I> conformational preferences were observed in the aromatic <I>N</I>, <I>N</I>'-dimethylated urea (4) and guanidine (7), in which two aromatic rings are located face-to-face. The <I>cis</I> conformations of <I>N</I>-methylated amides, ureas and guanidines could be utilized to construct interesting aromatic architecture. First, <I>N</I>, <I>N</I>', <I>N</I>″-trimethyl-<I>N</I>, <I>N</I>', <I>N</I>″-triphenyl-1, 3, 5-benzenetricarboxamide (12) and a cyclic triamide 14 have crystal structures in which three N-phenyl groups exist with the same orientation (<I>syn</I> conformation). Second, several aromatic amides which have no fixed asymmetric center afforded chiral crystals by simple recrystallization. In the case of 1, 2-bis (<I>N</I>-benzoyl-<I>N</I>-methylamino) benzene (18), two enantiomeric crystals could be distinguished morphologically or on the basis of symmetrical CD spectra in KBr, and by <SUP>1</SUP>H-NMR in the presence of chiral 1, 1'-bi-2-naphthol. Third, aromatic multi-layered structures could be constructed by using <I>N</I>, <I>N</I>'-dimethylated urea or guanidino bonds. These unique layered structures could be applied to obtain aromatic molecules with potent DNA-binding ability.

Journal

  • Journal of Synthetic Organic Chemistry, Japan

    Journal of Synthetic Organic Chemistry, Japan 58(6), 556-567, 2000-06-01

    The Society of Synthetic Organic Chemistry, Japan

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  • Stereochemistry of Benzanilides and N-Methylbenzanilides

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Codes

  • NII Article ID (NAID)
    10008820270
  • NII NACSIS-CAT ID (NCID)
    AN0024521X
  • Text Lang
    JPN
  • Article Type
    Journal Article
  • ISSN
    00379980
  • NDL Article ID
    5365265
  • NDL Source Classification
    ZP11(科学技術--化学・化学工業--有機化学・有機化学工業)
  • NDL Call No.
    Z17-256
  • Data Source
    CJP  CJPref  NDL  J-STAGE 
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