Multicomponent synthesis of unsymmetrical derivatives of 4-methyl-substituted 5-nitropyridines

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Multicomponent synthesis of unsymmetrical derivatives of 4-methyl-substituted 5-nitropyridines	1 MB	Adobe Acrobat PDF	Read	Download
DOI Доступ к ресурсу на сайте издателя			10.3390/pr11020576

Title: Multicomponent synthesis of unsymmetrical derivatives of 4-methyl-substituted 5-nitropyridines
Creator: Turgunalieva, Daria M.
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Stalinskaya, Alena L.
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Kulakov, Ilya I.
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Sagitullina, Galina P.
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Atuchin, Victor V.
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Elyshev, Andrey V.
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Kulakov, Ivan V.
Date: 2023
DOI: 10.3390/pr11020576
Description: 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.