Central European Journal of Chemistry

, Volume 3, Issue 2, pp 311–325 | Cite as

2-[3-(Trifluoromethyl)phenyl]furo[3,2-b]pyrroles: synthesis and reactions

  • Peter Gajdoš
  • Soňa Pavlíková
  • Filip Bureš
  • Alžbeta Krutošíková
Article
  • 86 Downloads

Abstract

The synthesis and reactions of methyl 2-[3-(trifluoromethyl)phenyl]-4H-furo[3,2-b]pyrrole-5-carboxylate (1a) are described. Upon reaction with methyl iodide, benzyl chloride, or acetic anhydride, this compound gave N-substituted products 1b-d. By hydrolysis of compounds 1a-c, the corresponding acids 2a-c were formed, or by reaction with hydrazine-hydrate, the corresponding carbohydrazides 3a-c were formed. By heating 2-[3-(trifluoromethyl)phenly]-4H-furo[3,2-b]pyrrole-5-carboxylic acid (2a) in acetic anhydride, 4-acetyl-2-[3-(trifluoromethyl)phenyl]furo[3,2-b]pyrrole (4) was formed. By hydrolysis of 4, 2-[3-(trifluoromethyl)phenyl]-4H-furo[3,2-b]pyrrole (5a) was formed, and reactions with methyl iodide or benzyl chloride gave N-substituted products 5b-c. The reaction of 4 with dimethyl butynedioate gave substituted benzo[b]furan 6. Compound 3a reacted with triethyl orthoesters giving 7a-c, which afforded with phosphorus (V) sulphide the corresponding thiones 8a-c. The thiones 8a-c reacted with hydrazine hydrate to form hydrazine derivatives 9a-c. The reaction of triethyl orthoformiate with compounds 9a-c led to furo[2′,3′: 4,5]pyrrolo[1,2-d][1,2,4]triazolo[3,4-f][1,2,4]triazines 10a-c. Hydrazones 11a-c were formed from 3a-c and 5-[3-(trifluoromethyl)phenyl]furan-2-carboxaldehyde. The effect of microwave irradiation on some condensation reactions was compared with “classical” conditions. The results showed that microwave irradiation shortens the reaction time while affording comparable yields.

Keywords

2-[3-(trifluoromethyl)phenyl]furo[3,2-b]pyrroles hydrazides hydrazones cycloaddition condensation phase transfer catalysis microwave irradiation 1H and13C NMR spectra 

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Copyright information

© Central European Science Journals 2005

Authors and Affiliations

  • Peter Gajdoš
    • 1
  • Soňa Pavlíková
    • 1
  • Filip Bureš
    • 2
  • Alžbeta Krutošíková
    • 1
  1. 1.Department of Chemistry of Faculty of Natural SciencesUniversity of St. Cyril and Methodius in TrnavaTrnavaSlovak Republic
  2. 2.Department of Organic Chemistry of Faculty of Chemical TechnologyUniversity of PardubicePardubiceCzech Republic

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