Synthesis and reactions of [1]benzofuro[3,2-c]pyridine

Authors

  • Nadežda Juristová Department of Chemistry, Faculty of Natural Sciences, University of SS. Cyril and Methodius, SK-917 01 Trnava, Slovak Republic
  • Eleonóra Štefanovová Department of Chemistry, Faculty of Natural Sciences, University of SS. Cyril and Methodius, SK-917 01 Trnava, Slovak Republic
  • Tatiana Ďurčeková Department of Chemistry, Faculty of Natural Sciences, University of SS. Cyril and Methodius, SK-917 01 Trnava, Slovak Republic
  • Naďa Prónayová Institute of Analytical Chemistry, Department of NMR and MS Spectroscopy, Slovak University of Technology, Radlinského 9, SK-812 37 Bratislava, Slovak Republic
  • Anton Gatial Institute of Physical Chemistry and Chemical Physics, Slovak University of Technology, Radlinského 9, SK-812 37 Bratislava, Slovak Republic
  • Alžbeta Krutošíková Department of Chemistry, Faculty of Natural Sciences, University of SS. Cyril and Methodius, SK-917 01 Trnava, Slovak Republic

DOI:

https://doi.org/10.36547/nbc.1366

Keywords:

[1]Benzofuro[3,2-c]pyridine, N-oxide, 1-carbonitrile, 1H, 13C NMR and IR spectra, metal-organic compounds

Abstract

(E)-3-(1-Benzofuran-2-yl)propenoic acid (I) was prepared from 1-benzofuran-2-carbaldehyde under the Doebner’s conditions. The obtained acid was converted to the corresponding azide II, which was cyclized by heating in diphenyl ether to [1]benzofuro[3,2-c]pyridin-1(2H)-one (III). This compound was aromatized with phosphorus oxychloride to chloroderivative IV which was reduced with zinc and acetic acid to the title compound V. [1]Benzofuro[3,2-c]pyridin-2-oxide (VI) was synthesized by reaction of V with 3-chloroperoxybenzoic acid in dichloromethane. Treatment VI with benzoyl chloride and potassium cyanide (Reissert-Henze reaction) was shown to produce the corresponding [1]benzofuro[3,2-c]pyridin-1-carbonitrile (VII). The title compound was used for preparation of complex compounds VIII, IX

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Published

2022-01-13

How to Cite

Juristová, N., Štefanovová, E., Ďurčeková, T., Prónayová, N., Gatial, A., & Krutošíková, A. (2022). Synthesis and reactions of [1]benzofuro[3,2-c]pyridine. Nova Biotechnologica Et Chimica, 7(1), 107–114. https://doi.org/10.36547/nbc.1366

Issue

Vol. 7 No. 1 (2007)

Section

Research Articles

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Copyright (c) 2022 Nadežda Juristová, Eleonóra Štefanovová, Tatiana Ďurčeková, Naďa Prónayová, Anton Gatial, Alžbeta Krutošíková

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