Multicomponent synthesis of 1,4-dihydropyridine-3,5-dicarbonitriles

Ryzhkova, Yuliya E.; Elinson, Michaïl N.

doi:10.24820/ark.5550190.p011.703

Arkivoc

2022

DOI: 10.24820/ark.5550190.p011.703

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Multicomponent synthesis of 1,4-dihydropyridine-3,5-dicarbonitriles

Yuliya E. Ryzhkova¹,

Michaïl N. Elinson²

Abstract: 1,4-Dihydropyridines are one of the most used classes of antihypertensive drugs. The present communication describes the autocatalytic four-component reaction of 2,6-dihalogen-substituted benzaldehydes, malononitrile and cyclic amines results in the formation of previously unknown 1,4-dihydropyridine-3,5dicarbonitriles. The structure of these previously unknown compounds was confirmed by means of 1 H and 13 C NMR and IR spectroscopy, mass spectrometry and elemental analysis.

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2023

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Cited by 2 publications

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Piperidine Derivatives: Recent Advances in Synthesis and Pharmacological Applications

Frolov

Vereshchagin

2023

IJMS

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Piperidines are among the most important synthetic fragments for designing drugs and play a significant role in the pharmaceutical industry. Their derivatives are present in more than twenty classes of pharmaceuticals, as well as alkaloids. The current review summarizes recent scientific literature on intra- and intermolecular reactions leading to the formation of various piperidine derivatives: substituted piperidines, spiropiperidines, condensed piperidines, and piperidinones. Moreover, the pharmaceutical applications of synthetic and natural piperidines were covered, as well as the latest scientific advances in the discovery and biological evaluation of potential drugs containing piperidine moiety. This review is designed to help both novice researchers taking their first steps in this field and experienced scientists looking for suitable substrates for the synthesis of biologically active piperidines.

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Piperidine Derivatives: Recent Advances in Synthesis and Pharmacological Applications

Frolov

Vereshchagin

2023

IJMS

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

et al. 2023

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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.

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Multicomponent synthesis of 1,4-dihydropyridine-3,5-dicarbonitriles

Cited by 2 publications

References 23 publications

Piperidine Derivatives: Recent Advances in Synthesis and Pharmacological Applications

Piperidine Derivatives: Recent Advances in Synthesis and Pharmacological Applications

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

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