Reaction of Pyridoxal with Phenols: Synthesis of Novel 1-Aryl-Substituted Furopyridines

Ludmila K. Kibardina; Ludmila V. Chumakova; Almir S. Gazizov; Alexander R. Burilov; Michail A. Pudovik

doi:10.1055/s-0034-1378684

Synthesis, Inhaltsverzeichnis

Synthesis 2015; 47(05): 721-725
DOI: 10.1055/s-0034-1378684

paper

Reaction of Pyridoxal with Phenols: Synthesis of Novel 1-Aryl-Substituted Furopyridines

Ludmila K. Kibardina

^aA. E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center, Russian Academy of Sciences, Arbuzov str. 8, Kazan 420088, Russian Federation

,

Ludmila V. Chumakova

^bKazan State Technology University, K. Marks str. 68, Kazan 420015, Russian Federation eMail: agazizov@iopc.ru

,

Almir S. Gazizov*

^aA. E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center, Russian Academy of Sciences, Arbuzov str. 8, Kazan 420088, Russian Federation

,

Alexander R. Burilov

^aA. E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center, Russian Academy of Sciences, Arbuzov str. 8, Kazan 420088, Russian Federation

,

Michail A. Pudovik

^aA. E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center, Russian Academy of Sciences, Arbuzov str. 8, Kazan 420088, Russian Federation

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Abstract

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Abstract

A new method based on the acid-catalyzed reaction of pyridoxal with polyfunctional phenols has been developed for the synthesis of potentially biologically active 1-aryl-6-methyl-1,3-dihydrofuro[3,4-c]pyridin-7-ols. Advantages of this method include a good yield of the target furopyridines and the use of readily available hydrochloric acid as a catalyst. The possibility of extending the proposed approach to nucleophiles other than phenols was demonstrated by the synthesis of the known biologically active compound 1-(5-hydroxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)-6-methyl-1,3-dihydrofuro[3,4-c]pyridin-7-ol hydrochloride (TM2002).

Key words

phenols - furans - pyridines - aldehydes - polycycles - heterocycles

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Referenzen

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