Reactions of 5-[3-(trifluoromethyl)phenyl]furan-2-carbaldehyde

被引：1
|
作者：
Gajdos, P. [1 ]
Miklovic, J. [1 ]
Krutosikova, A. [1 ]
机构：
[1] Univ St Cyril & Methodius, Fac Nat Sci, SK-91701 Trnava, Slovakia
来源：
KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII | 2006年 / 06期
关键词：
methyl 2-[3-(trifluoromethyl)phenyl)]-4H-furo[3,2-b]pyrrole-5-carboxylate; 5-[3-(trifluoromethyl)phenyl]furan-2-carbaldehyde; 2-[3-(trifluoromethyl)phenyl)]furo[3,2-c]pyridine; Knoevenagel reaction;
D O I：
暂无
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The Knoevenagel condensations of 5-[3-(trifluoromethyl)phenyl]furan-2-carbaldehyde with seven compounds containing an active methyl or methylene group have been studied. The compounds used were: methyl 2-cyanoacetate, malononitrile, 2-furylacetonitrile, acetophenone, 2-thioxo-1,3-thiazolidin-4-one (rhodanine), 5,5-dimethylcyclohexane-1,3-dione (dimedone) and methyl 2-azidoacetate. The effect of microwave irradiation on the condensation reactions was studied and compared with "classical" conditions. Thermolysis of methyl 2-azido-3-{5-[3(trifluoromethyl)phenyl]-2-furyl}propenoate afforded methyl 2-[3-(trifluoromethyl)phenyl]-4H-furo[3,2-b]pyrrole-5-carboxylate. (2E)-3-{5-[3-(Trifluoromethyl)phenyl]-2-furyl}propenoic acid was converted to corresponding azide, which was cyclized on heating into 2-[3-(trifluoromethyl)phenyl]-4,5-dihydrofuro[3,2-c]pyridin-4-one. The latter after successive action of POCl3 and NH2NH2-Pd/C gave 2-[3-(trifluoromethyl)phenyl]furo[3,2-c]pyridine.
引用
收藏
页码：825 / 831
页数：7
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