作者:István Lengyel、Victor Cesare、Tony Taldone
DOI:10.1016/j.tet.2003.11.067
日期:2004.1
α-Lactams (aziridinones) can function to replace two of the three reactants, the oxo-compound and the isonitrile, in the Passerini reaction. Four α-lactams (5a-d) were reacted with mono- and dicarboxylic acids of positive pKa values to give 2-acyloxycarboxamides (4) and bis-2-acyloxycarboxamide products 12 and 13, respectively. The same compounds were also prepared via the Passerini reaction. Acids
α-内酰胺(叠氮ino烷)可以在Passerini反应中取代三种反应物中的两种,即氧代化合物和异腈。使四个α-内酰胺(5a - d)与正p K a值的单羧酸和二羧酸反应,分别得到2-酰氧基羧酰胺(4)和双-2-酰氧基羧酰胺产物12和13。还通过Passerini反应制备了相同的化合物。p K a p为负的酸将α-内酰胺脱羰,生成铵盐。反应的主要路径取决于p K a 酸成分,α-内酰胺的反应性和反应条件。