Functional Derivatives of 4-Formyl-2-methoxyphenyl Pyridine-4-carboxylate

Acylation of vanillin with isonicotinoyl chloride gave 4-formyl-2-methoxyphenyl pyridine-4-carboxylate which was converted into a number of functional derivatives, including those containing isoxazole and isothiazole heterocycles. In particular, the condensation of the title compound with primary am...

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Bibliographic Details
Published in:Russian journal of organic chemistry 2019-10, Vol.55 (10), p.1483-1494
Main Authors: Potkin, V. I., Bumagin, N. A., Dikusar, E. A., Petkevich, S. K., Kurman, P. V.
Format: Article
Language:English
Subjects:
Acylation
Amides
Amines
Carbonyls
Catalytic activity
Chemical reactions
Chemistry
Chemistry and Materials Science
Chlorides
Derivatives
Esters
Imines
Organic Chemistry
Palladium
Phosgene
Vanillin
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Summary:Acylation of vanillin with isonicotinoyl chloride gave 4-formyl-2-methoxyphenyl pyridine-4-carboxylate which was converted into a number of functional derivatives, including those containing isoxazole and isothiazole heterocycles. In particular, the condensation of the title compound with primary amines afforded the corresponding Schiff bases. 4-Formyl-2-methoxyphenyl pyridine-4-carboxylate and one of the Schiff bases derived therefrom were reduced with sodium triacetoxohydridoborate to the corresponding alcohol and amine which were acylated with 5-arylisoxazole- and 4,5-dichloroisothiazole-3-carbonyl chlorides to obtain esters and amides having isoxazole and isothiazole fragments. The synthesized compounds readily formed complexes with palladium(II) chloride, which showed a high catalytic activity in the Suzuki reaction of 3-bromobenzoic acid with 4-methoxyphenylboronic acid in water in the absence of an organic solvent.
ISSN:1070-4280
1608-3393
DOI:10.1134/S1070428019100063