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[1]Benzofuro[3,2-c]pyridine synthesis and coordination reactions

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Abstract

(E)-3-(1-Benzofuran-2-yl)propenoic acid (1) was prepared from 1-benzofuran-2-carbaldehyde under the Doebner’s conditions. The obtained acid was converted to the corresponding azide 2, which was cyclized by heating in diphenyl ether to [1]benzofuro[3,2-c]pyridine-1(2H)-one (3). This compound was aromatized with phosphorus oxychloride to chloroderivative 4 which was reduced with zinc and acetic acid to the title compound 5. [1]Benzofuro[3,2-c]pyridine-2-oxide (6) was synthesized by reaction of 5 with 3-chloroperoxybenzoic acid in dichloromethane. Treatment of 6 with benzoyl chloride and potassium cyanide (Reissert-Henze reaction) was shown to produce the corresponding [1]benzofuro[3,2-c]pyridine-1-carbonitrile (7). The title compound was used for preparation of complexes Cu2(ac)4(bfp)2 (8) and CoCl2(bfp)2 (9), where ac=CH3CO −2 and bfp=[1]benzofuro[3,2-c]pyridine. Both oxygen atom of carboxylate ions is used in the coordination to Cu(II). Thermal properties of the complexes 8 and 9 have been studied by TG and DTA and both complexes exhibited high thermal stability while complex 9 are thermally more stable than complex 8.

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Authors and Affiliations

  1. Department of Chemical Engineering and Applied Chemistry, University of Toronto, 200 College Street, Toronto, ON, M5S 3E5, Canada

    S. C. Mojumdar

  2. Department of Engineering, University of New Brunswick, Saint John, NB, E2L 4L5, Canada

    S. C. Mojumdar

  3. Institute of Physical Chemistry and Chemical Physics, Slovak University of Technology, Radlinského 9, 812 37, Bratislava, Slovakia

    P. Šimon

  4. Department of Chemistry, Faculty of Natural Sciences, University of Ss. Cyril and Methodius, 917 01, Trnava, Slovakia

    A. Krutošíková

Authors
  1. S. C. Mojumdar
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  2. P. Šimon
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  3. A. Krutošíková
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Correspondence to S. C. Mojumdar.

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Mojumdar, S.C., Šimon, P. & Krutošíková, A. [1]Benzofuro[3,2-c]pyridine synthesis and coordination reactions. J Therm Anal Calorim 96, 103–109 (2009). https://doi.org/10.1007/s10973-008-9881-6

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