Open AccessSynthesis and reactions of [1]benzofuro[3,2-c]pyridine
Author(s) -
Nadežda Juristová,
Eleonóra Štefanovová,
Tatiana Ďurčeková,
Naďa Prónayová,
A. Gatial,
A. Krutošíková
Publication year - 2022
Publication title -
nova biotechnologica et chimica
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.212
H-Index - 9
eISSN - 1339-004X
pISSN - 1338-6905
DOI - 10.36547/nbc.1366
Subject(s) - chemistry , pyridine , benzofuran , acetic acid , medicinal chemistry , potassium cyanide , phosphorus pentoxide , benzoyl chloride , dichloromethane , salicylaldehyde , organic chemistry , phosphorus pentachloride , diphenyl ether , potassium thiocyanate , nuclear chemistry , cyanide , solvent , polymer chemistry , schiff base
(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