Multicomponent Synthesis of Unsymmetrical Derivatives of 4-Methyl-Substituted 5-Nitropyridines.

Autor: Turgunalieva, Daria M., Stalinskaya, Alena L., Kulakov, Ilya I., Sagitullina, Galina P., Atuchin, Victor V., Elyshev, Andrey V., Kulakov, Ivan V.
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Zdroj: Processes; Feb2023, Vol. 11 Issue 2, p576, 12p
Abstrakt: The multicomponent reaction of 2-nitroacetophenone (or nitroacetone), acetaldehyde diethyl acetal, β-dicarbonyl compound, and ammonium acetate in an acetic acid solution allowed the acquisition of previously undescribed 4-methyl-substituted derivatives of 5-nitro-1,4-dihydropyridine in satisfactory yields. The oxidation of the obtained 5-nitro-1,4-dihydropyridine derivatives resulted in the corresponding 2,4-dimethyl-5-nitropyridines. In addition, for the first time in the synthesis of unsymmetrical 1,4-dihydropyridines by the Hantzsch reaction acetaldehyde, diethyl acetal was used as a source of acetaldehyde. The use of more volatile and sufficiently reactive acetaldehyde in this reaction did not lead to a controlled synthesis of unsymmetrical 5-nitro-1,4-dihydropyridines. The proposed multicomponent approach to the synthesis of 4-methyl-substituted 5-nitro-1,4-dihydropyridines and their subsequent aromatization into pyridines made it possible to obtain previously undescribed and hardly accessible substituted 5(3)-nitropyridines. [ABSTRACT FROM AUTHOR]
Databáze: Complementary Index