Division of Chemistry and Biotechnology, Graduate School of Natural Science and Technology, Okayama University, 3-1-1 Tsushimanaka, Okayama 700-8530, Japan.
Org Lett. 2012 Jun 15;14(12):3182-5. doi: 10.1021/ol301273j. Epub 2012 May 31.
A new method is described for the regioselective synthesis of multisubstituted pyridine derivatives. Treatment of N-acetyl β-enamino ketones with alkynes in the presence of the rhenium catalyst, Re(2)(CO)(10), gives multisubstituted pyridines regioselectively. In this reaction, the N-acetyl moieties are important for the selective formation of the multisubstituted pyridines. This reaction proceeds via insertion of alkynes into a carbon-carbon single bond of β-enamino ketones, intramolecular nucleophilic cyclization, and elimination of acetic acid.
介绍了一种区域选择性合成多取代吡啶衍生物的新方法。在铼催化剂 Re(2)(CO)(10)的存在下，用炔烃处理 N-乙酰基β-烯胺酮，可以选择性地得到多取代吡啶。在这个反应中，N-乙酰基对于选择性形成多取代吡啶是很重要的。该反应通过炔烃插入β-烯胺酮的碳-碳单键、分子内亲核环化和乙酸消除进行。
