REACTIONS OF 5-[3-(TRIFLUOROMETHYL)PHENYL]FURAN-2-CARBALDEHYDE

Authors

  • P. Gajdoš Department of Chemistry, Faculty of Natural Sciences, University of St. Cyril and Methodius in Trnava, SK-917 01 Trnava
  • J. Miklovič Department of Chemistry, Faculty of Natural Sciences, University of St. Cyril and Methodius in Trnava, SK-917 01 Trnava
  • A. Krutošíková Department of Chemistry, Faculty of Natural Sciences, University of St. Cyril and Methodius in Trnava, SK-917 01 Trnava

DOI:

https://doi.org/10.1007/7944

Keywords:

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

Abstract

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.

How to Cite
Gajdoš, P.; Miklovič, J.; Krutošíková, A.  Chem. Heterocycl. Compd. 2006, 42, 719. [Khim. Geterotsikl. Soedin. 2006, 825.]

For this article in the English edition see DOI 10.1007/s10593-006-0151-x

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Published

2023-08-14

Issue

No. 6 (2006)

Section

Original Papers