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Keywords = nitroacetone

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12 pages, 1235 KiB  
Article
Multicomponent Synthesis of Unsymmetrical Derivatives of 4-Methyl-Substituted 5-Nitropyridines
by Daria M. Turgunalieva, Alena L. Stalinskaya, Ilya I. Kulakov, Galina P. Sagitullina, Victor V. Atuchin, Andrey V. Elyshev and Ivan V. Kulakov
Processes 2023, 11(2), 576; https://doi.org/10.3390/pr11020576 - 14 Feb 2023
Cited by 7 | Viewed by 2630
Abstract
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 [...] Read more.
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. Full article
(This article belongs to the Section Chemical Processes and Systems)
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