Synthesis 2015; 47(05): 721-725
DOI: 10.1055/s-0034-1378684
paper
© Georg Thieme Verlag Stuttgart · New York

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

Ludmila K. Kibardina
a  A. 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
b  Kazan State Technology University, K. Marks str. 68, Kazan 420015, Russian Federation   Email: agazizov@iopc.ru
,
Almir S. Gazizov*
a  A. 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
a  A. 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
a  A. E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center, Russian Academy of Sciences, Arbuzov str. 8, Kazan 420088, Russian Federation
› Author Affiliations
Further Information

Publication History

Received: 22 September 2014

Accepted after revision: 17 November 2014

Publication Date:
15 December 2014 (eFirst)

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).

Supporting Information

 
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