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Chemistry of Heterocyclic Compounds

, Volume 42, Issue 6, pp 719–725 | Cite as

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

  • P. Gajdos
  • J. Miklovic
  • A. Krutosikova
Article

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 the 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.

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 

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Copyright information

© Springer Science+Business Media, Inc. 2006

Authors and Affiliations

  • P. Gajdos
    • 1
  • J. Miklovic
    • 1
  • A. Krutosikova
    • 1
  1. 1.Department of Chemistry, Faculty of Natural SciencesUniversity of St. Cyril and Methodius in TrnavaTrnavaSlovak Republic

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