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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
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Document type:
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Článok z časopisu / Journal Article |
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Collection:
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Chemical papers
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| Author(s) |
Búdová, M.
Fojtíková, K.
Miklovič, J.
Mrázová, V.
Horváth, B.
Krutošíková, A.
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| Title |
Synthesis and reactions of 2-and 4-substituted furo[3,2-c]pyridines
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| Journal name |
Chemical Papers
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| Publication date |
2006
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| Year available |
2006
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| Volume number |
60
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| Issue number |
3
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| ISSN |
0366-6352
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| Start page |
231
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| End page |
236
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| Place of publication |
Poland
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| Publisher |
Versita
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| Collection year |
2006
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| Language |
english
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| Subject |
250000 Chemical Sciences
250300 Organic Chemistry
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| 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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