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Efficient syntheses of macrocycles ranging from 22-28 atoms through spontaneous dimerization to yield bis-hydrazones

机译：通过自发二聚体产生22-28个原子的高效合成宏细胞，以产生双腙

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摘要

Acid treatment of a triazine displaying both a tethered acetal and BOC-protected hydrazine group leads to spontaneous condensation to yield macrocyclic dimers in excellent yields and purity. The bis-triazinyl hydrazones that form are characterized by H-1-NMR, C-13-NMR, H-1-COSY spectroscopy, X-ray diffraction, and mass spectrometry. By varying the length of the tether-the condensation product of an amino acid and amino acetal-rings comprising 22-28 atoms can be accessed. Glycine and beta-alanine were used for the amino acid. The amino acetal comprised 2, 3 or 4 carbon atoms in the backbone. High-performance liquid chromatography (HPLC) was employed to assess purity as well as to fingerprint the six homodimeric products. By combining the protected monomers and subjecting them to acid, mixtures of homodimers and heterodimers are obtained. When all six protected monomers are combined, at least 14 of the 21 theoretical dimeric products are observed by HPLC. Single crystal X-ray diffraction and solution NMR studies reveal the diversity of shapes available to these molecules.
机译：酸治疗三嗪显示束缚缩醛和Boc保护的肼基团，导致自发缩合，以产生优异的产率和纯度的大环二聚体。该形式的双三唑腙的特征在于H-1-NMR，C-13-NMR，H-1-舒适的光谱，X射线衍射和质谱。通过改变系绳的长度 - 可以进入包含22-28个原子的氨基酸和氨基缩醛环的缩合产物。甘氨酸和β-丙氨酸用于氨基酸。氨基缩醛在骨架中包含2,3或4个碳原子。使用高效液相色谱（HPLC）来评估纯度以及指纹六种同源二聚体产物。通过组合保护的单体并使它们进行酸，获得同源体和异二聚体的混合物。当组合所有六种受保护的单体时，通过HPLC观察到21种理论二聚体产品中的至少14个。单晶X射线衍射和溶液NMR研究揭示了这些分子可用的形状的多样性。

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  • 来源
    《RSC Advances》 |2020年第6期|共4页
  • 作者

    Sharma Vishal R.; Mehmood Arshad; Janesko Benjamin G.; Simanek Eric E.;

  • 作者单位

    Texas Christian Univ Dept Chem &

    Biochem Ft Worth TX 76129 USA;

    Texas Christian Univ Dept Chem &

    Biochem Ft Worth TX 76129 USA;

    Texas Christian Univ Dept Chem &

    Biochem Ft Worth TX 76129 USA;

    Texas Christian Univ Dept Chem &

    Biochem Ft Worth TX 76129 USA;

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  • 正文语种 eng
  • 中图分类 化学;
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