Synthesis and reactions of 2-and 4-substituted furo[3,2-c]pyridines

Búdová, M., Fojtíková, K., Miklovič, J., Mrázová, V., Horváth, B. and Krutošíková, A. Synthesis and reactions of 2-and 4-substituted furo[3,2-c]pyridines Chemical Papers, Vol.60, No. 3, 2006, 231-236

Document type: Článok z časopisu / Journal Article
Collection: Chemical papers  

Author(s) Búdová, M.
Fojtíková, K.
Miklovič, J.
Mrázová, V.
Horváth, B.
Krutošíková, A.
Title Synthesis and reactions of 2-and 4-substituted furo[3,2-c]pyridines
Journal name Chemical Papers
Publication date 2006
Year available 2006
Volume number 60
Issue number 3
ISSN 0366-6352
Start page 231
End page 236
Place of publication Poland
Publisher Versita
Collection year 2006
Language english
Subject 250000 Chemical Sciences
250300 Organic Chemistry
Abstract/Summary Substituted furopropenoic acids were prepared from appropriate aldehyde under the Doebner’s conditions. Obtained acids were converted to the corresponding azides, which were cyclized by heating in Dowtherm to furopyridones. These compounds were aromatized with phosphorus oxychloride to chloro derivatives of furo[3,2-c]pyridine (Va, Vb). Chloro derivative Vb was reduced with hydrazine hydrate to 2-(4-aminophenyl)furo[3,2-c]pyridine in ethanol and Pd/C as a catalyst. Chloro derivative Va was converted to 4-amino-2-(3-pyridyl)furo[3,2-c]pyridine under the same conditions. The chlorine atom in other chloro derivatives (VIIa, VIIb) was replaced by nucleophilic substitution with alkoxides (sodium ethoxide, propoxide, and isopropoxide) and the corresponding alkoxy derivatives were formed. By reaction of VII with cyclic secondary amines (morpholine, piperidine, and pyrrolidine) 4-substituted furopyridines were prepared.
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Created: Tue, 16 Mar 2010, 13:13:41 CET by Iveta Drtilová . Detailed History