FeCl3-Assisted Niobium-Catalyzed Cycloaddition of Nitriles and Alkynes: Synthesis of Alkyl- and Arylpyrimidines Based on Independent Functions of NbCl5 and FeCl3 Lewis Acids

被引:41
作者
Fuji, Maito [1 ]
Obora, Yasushi [1 ]
机构
[1] Kansai Univ, Dept Chem & Mat Engn, Fac Chem Mat & Bioengn, Suita, Osaka 5648680, Japan
关键词
INTERMOLECULAR 2+2+2 CYCLOADDITION; 2 DISCRETE NITRILES; ONE-STEP SYNTHESIS; ONE-POT SYNTHESIS; PYRIMIDINE-DERIVATIVES; MULTICOMPONENT REACTION; PYRIDINE-DERIVATIVES; ORGANIC-SYNTHESIS; INTERNAL ALKYNES; TERMINAL ALKYNES;
D O I
10.1021/acs.orglett.7b02708
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
NbCl5-catalyzed [2 + 2 + 2] cycloaddition of nitriles with alkynes was used to synthesize pyrimidine derivatives. In this reaction, the use of individual Lewis acids, namely NbCl5 and FeCl3, is a key strategy for achieving the reaction using a catalytic amount of NbCl5. The roles of the two Lewis acids were investigated using FT-IR spectroscopy. The results showed that NbCl5 served as an efficient Lewis acid catalyst for nitrile activation, whereas FeCl3 showed stronger Lewis acidity toward pyrimidines, releasing NbCl5 into the catalytic cycle.
引用
收藏
页码:5569 / 5572
页数:4
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