Tris(o-phenylenedioxy)cyclotriphosphazene as a Promoter for the Formation of Amide Bonds Between Aromatic Acids and Amines
Tris(o-phenylenedioxy)cyclotriphosphazene as a Promoter for the Formation of Amide Bonds Between Aromatic Acids and Amines
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DOI：
10.1055/s-0040-1707174
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发表时间：
2020-11-03
影响因子：
2.6
通讯作者：
Saito, Susumu
中科院分区：
文献类型：
--
作者：
Movahed, Farzaneh Soleymani;Sawant, Dinesh N.;Saito, Susumu
酰胺键的原子效率形成已成为有机合成中的首要研究领域，因为酰胺键构成蛋白质的主链并代表药物分子中的重要结构基序。目前，对该领域新发现的需求不断增加，人们对这一具有挑战性的课题给予了极大的关注。在此，可降解的1,3,5-三氮基-2,4,6-三磷碱（TAP）基序被提出作为一种新的缩合系统，用于在芳香族羧酸和胺的不同组合之间脱水形成酰胺键。研究了潜在的反应机理，并使用 (31)P NMR 光谱和 ESI 质谱对潜在的催化剂中间体进行了表征。
The atom-efficient formation of amide bonds has emerged as a top-priority research field in organic synthesis, as amide bonds constitute the backbones of proteins and represent an important structural motif in drug molecules. Currently, the increasing demand for novel discoveries in this field has focused substantial attention on this challenging subject. Herein, the degradable 1,3,5-triazo-2,4,6-triphosphorine (TAP) motif is presented as a new condensation system for the dehydrative formation of amide bonds between diverse combinations of aromatic carboxylic acids and amines. The underlying reaction mechanism was investigated, and potential catalyst intermediates were characterized using(31)P NMR spectroscopy and ESI mass spectrometry.