Use of the Curtius Rearrangement of Acryloyl Azides in the Synthesis of 3,5-Disubstituted Pyridines: Mechanistic Studies
作者:Ta-Hsien Chuang、Yu-Chi Chen、Someshwar Pola
DOI:10.1021/jo101394c
日期:2010.10.1
A series of disubstituted pyridine derivatives was synthesized from the corresponding acryloyl azides by acetic acid-promoted cycloaddition. This represents a novel and convenient synthetic approach to the symmetric 3,5-disubstituted pyridines. The nature of the substituent on the double bond and the utilized solvent were found to be crucial to the yield of pyridines. The reactivity of the acid-promoted
通过乙酸促进的环加成反应,由相应的丙烯酰基叠氮化物合成了一系列双取代的吡啶衍生物。这代表了对称的3,5-二取代吡啶的新颖且方便的合成方法。发现双键上取代基的性质和所用溶剂对吡啶的产率至关重要。酸促进的环加成反应的反应性随芳基(例如苯基和吡啶基)的存在而增加。我们还通过13 C标记的肉桂酰叠氮化物的酸促进的环加成反应探索了全面的机理。由丙烯酰基叠氮化物通过乙酸促进的三分子缩合合成对称的3,5-二取代的吡啶。