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
Highlights
Furopyridines are of chemical interest due to their similarity to quinoline, isoquinoline, and benzofuran, which are important ring systems present in many biologically active compounds
Furo[3,2-c]pyridine and its 2-methyl, 2,3-dimethyl and benzo[4,5] derivative were used for the first time as ligands to synthesize potentially new Werner clathrates and their structural characterization, spectral and magnetic properties of isothiocyanate nickel(II) complexes (MIKLOVIČ et al, 2004, MOJUMDAR et al, 2005)
In this paper, which continues our previous papers (BENCKOVÁ and KRUTOŠÍKOVÁ, 1999; KRUTOŠÍKOVÁ et al, 1992, 1994, 1995) we report the synthesis of [1]benzofuro[3,2-c]pyridine and its 2-oxide (Scheme 1)
Summary
Furopyridines are of chemical interest due to their similarity to quinoline, isoquinoline, and benzofuran, which are important ring systems present in many biologically active compounds. The antihypertensitive drug cicletanine is a furo[3,2c]pyridine derivative. The authors (BENCKOVÁ and KRUTOŠÍKOVÁ, 1995; 1999) were concentrated on transformations on the pyridine ring of some of this type of compounds. Later on some furo[3,2-c]pyridines have been used for preparation Cu(II) and Ni(II) complexes (KRUTOŠÍKOVÁ et al, 2001). Furo[3,2-c]pyridine and its 2-methyl-, 2,3-dimethyl and benzo[4,5] derivative were used for the first time as ligands to synthesize potentially new Werner clathrates and their structural characterization, spectral and magnetic properties of isothiocyanate nickel(II) complexes (MIKLOVIČ et al, 2004, MOJUMDAR et al, 2005). C]pyridinecopper(II) and bis(1-benzofuro[3,2-c]pyridine-κN)dichlorocobalt(II) were published (VRABEL et al, 2007). In this paper, which continues our previous papers (BENCKOVÁ and KRUTOŠÍKOVÁ, 1999; KRUTOŠÍKOVÁ et al, 1992, 1994, 1995) we report the synthesis of [1]benzofuro[3,2-c]pyridine and its 2-oxide (Scheme 1)
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