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Pyridine carboxaldehyde-based synthesis of oxygen-containing heterocycles

✍ Scribed by U. G. Ibatullin; T. F. Petrushina; L. Ya. Leitis; I. N. Plesanova; R. A. Skolmeistere; M. V. Shimanskaya; M. G. Safarov

Publisher: Springer US
Year: 1989
Tongue: English
Weight: 308 KB
Volume: 25
Category: Article
ISSN: 0009-3122
DOI: 10.1007/bf00470026

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✦ Synopsis

Heterocycles containing one or two atoms of oxygen are synthesized by the condensation of pyridine carboxaldehydes with ethylene glycol, 1,3-propanediol, and 3-methyl-3-buten-l-ol.

When the unsaturated alcohol is used, linear acetals are formed along with the cyclic products.

Pyridine and oxygen-containing heterocycles enter into the composition of many natural and synthetic, biologically active substances~ Compounds are also known containing both of these fragments in a single molecule, such as derivatives of 5-hydroxy-2-pyridyl-l,3dioxanes, that possess antimicrobial and antifungal activity [i]. This gives grounds for considering similar polyheterocycles as potentially biologically active substances.

In the present work, it is shown possible to obtain pyridine-containing derivatives of dioxolane, dioxane, and dihydropyran by the condensation of ethylene glycol (I), 1,3-propanediel (II), and 3-methyl-3-buten-l-ol (III), respectively, with 2-, 3-, and 4-pyridine carboxaldehyde (IVa-c)~

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