Oxidative aromatization of 4,7-dihydro-6-nitroazolo[1,5-a] pyrimidines: Synthetic possibilities and limitations, mechanism of destruction, and the theoretical and experimental substantiation

Daniil N. Lyapustin; Evgeny N. Ulomsky; Ilya A. Balyakin; Alexander V. Shchepochkin; Vladimir L. Rusinov; Oleg N. Chupakhin

doi:10.3390/molecules26164719

Oxidative aromatization of 4,7-dihydro-6-nitroazolo[1,5-a] pyrimidines: Synthetic possibilities and limitations, mechanism of destruction, and the theoretical and experimental substantiation

Daniil N. Lyapustin
, Evgeny N. Ulomsky
, Ilya A. Balyakin
, Alexander V. Shchepochkin
, Vladimir L. Rusinov^*
, Oleg N. Chupakhin

^*Corresponding author for this work

Ural Federal University
Ural Branch of the Russian Academy of Sciences
Institute of Metallurgy of the Ural Branch of the Russian Academy of Sciences

Research output: Contribution to journal › Article › peer-review

12 Scopus citations

Abstract

The reaction tolerance of the multicomponent process between 3-aminoazoles, 1-morpholino2-nitroalkenes, and aldehydes was studied. The main patterns of this reaction have been established. Conditions for the oxidation of 4,7-dihydro-6-nitroazolo[1,5-a]pyrimidines were selected. Previous claims that the 4,7-dihydro-6-nitroazolo[1,5-a]pyrimidines could not be aromatised have now been refuted. Compounds with an electron-donor substituent at position seven undergo decomposition during oxidation. The phenomenon was explained based on experimental data, electro-chemical experiment, and quantum-chemical calculation. The mechanism of oxidative degradation has been proposed.

Original language	English
Article number	4719
Journal	Molecules
Volume	26
Issue number	16
DOIs	https://doi.org/10.3390/molecules26164719
State	Published - 2 Aug 2021
Externally published	Yes

Keywords

Azolo[1,5-a]pyrimidines
Multicomponent reactions
Nitro compounds
Nitro-synthons
Oxidation
Oxidative destruction
Synthesis of heterocycles

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10.3390/molecules26164719

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Lyapustin, D. N., Ulomsky, E. N., Balyakin, I. A., Shchepochkin, A. V., Rusinov, V. L., & Chupakhin, O. N. (2021). Oxidative aromatization of 4,7-dihydro-6-nitroazolo[1,5-a] pyrimidines: Synthetic possibilities and limitations, mechanism of destruction, and the theoretical and experimental substantiation. Molecules, 26(16), Article 4719. https://doi.org/10.3390/molecules26164719

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title = "Oxidative aromatization of 4,7-dihydro-6-nitroazolo[1,5-a] pyrimidines: Synthetic possibilities and limitations, mechanism of destruction, and the theoretical and experimental substantiation",

abstract = "The reaction tolerance of the multicomponent process between 3-aminoazoles, 1-morpholino2-nitroalkenes, and aldehydes was studied. The main patterns of this reaction have been established. Conditions for the oxidation of 4,7-dihydro-6-nitroazolo[1,5-a]pyrimidines were selected. Previous claims that the 4,7-dihydro-6-nitroazolo[1,5-a]pyrimidines could not be aromatised have now been refuted. Compounds with an electron-donor substituent at position seven undergo decomposition during oxidation. The phenomenon was explained based on experimental data, electro-chemical experiment, and quantum-chemical calculation. The mechanism of oxidative degradation has been proposed.",

keywords = "Azolo[1,5-a]pyrimidines, Multicomponent reactions, Nitro compounds, Nitro-synthons, Oxidation, Oxidative destruction, Synthesis of heterocycles",

author = "Lyapustin, \{Daniil N.\} and Ulomsky, \{Evgeny N.\} and Balyakin, \{Ilya A.\} and Shchepochkin, \{Alexander V.\} and Rusinov, \{Vladimir L.\} and Chupakhin, \{Oleg N.\}",

note = "Publisher Copyright: {\textcopyright} 2021 by the authors. Licensee MDPI, Basel, Switzerland.",

year = "2021",

month = aug,

day = "2",

doi = "10.3390/molecules26164719",

language = "英语",

volume = "26",

journal = "Molecules",

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number = "16",

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Oxidative aromatization of 4,7-dihydro-6-nitroazolo[1,5-a] pyrimidines: Synthetic possibilities and limitations, mechanism of destruction, and the theoretical and experimental substantiation. / Lyapustin, Daniil N.; Ulomsky, Evgeny N.; Balyakin, Ilya A. et al.
In: Molecules, Vol. 26, No. 16, 4719, 02.08.2021.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

T1 - Oxidative aromatization of 4,7-dihydro-6-nitroazolo[1,5-a] pyrimidines

T2 - Synthetic possibilities and limitations, mechanism of destruction, and the theoretical and experimental substantiation

AU - Lyapustin, Daniil N.

AU - Ulomsky, Evgeny N.

AU - Balyakin, Ilya A.

AU - Shchepochkin, Alexander V.

AU - Rusinov, Vladimir L.

AU - Chupakhin, Oleg N.

PY - 2021/8/2

Y1 - 2021/8/2

N2 - The reaction tolerance of the multicomponent process between 3-aminoazoles, 1-morpholino2-nitroalkenes, and aldehydes was studied. The main patterns of this reaction have been established. Conditions for the oxidation of 4,7-dihydro-6-nitroazolo[1,5-a]pyrimidines were selected. Previous claims that the 4,7-dihydro-6-nitroazolo[1,5-a]pyrimidines could not be aromatised have now been refuted. Compounds with an electron-donor substituent at position seven undergo decomposition during oxidation. The phenomenon was explained based on experimental data, electro-chemical experiment, and quantum-chemical calculation. The mechanism of oxidative degradation has been proposed.

AB - The reaction tolerance of the multicomponent process between 3-aminoazoles, 1-morpholino2-nitroalkenes, and aldehydes was studied. The main patterns of this reaction have been established. Conditions for the oxidation of 4,7-dihydro-6-nitroazolo[1,5-a]pyrimidines were selected. Previous claims that the 4,7-dihydro-6-nitroazolo[1,5-a]pyrimidines could not be aromatised have now been refuted. Compounds with an electron-donor substituent at position seven undergo decomposition during oxidation. The phenomenon was explained based on experimental data, electro-chemical experiment, and quantum-chemical calculation. The mechanism of oxidative degradation has been proposed.

KW - Azolo[1,5-a]pyrimidines

KW - Multicomponent reactions

KW - Nitro compounds

KW - Nitro-synthons

KW - Oxidation

KW - Oxidative destruction

KW - Synthesis of heterocycles

UR - https://www.scopus.com/pages/publications/85112029923

U2 - 10.3390/molecules26164719

DO - 10.3390/molecules26164719

M3 - 文章

C2 - 34443304

AN - SCOPUS:85112029923

SN - 1420-3049

VL - 26

JO - Molecules

JF - Molecules

IS - 16

M1 - 4719

ER -

Oxidative aromatization of 4,7-dihydro-6-nitroazolo[1,5-a] pyrimidines: Synthetic possibilities and limitations, mechanism of destruction, and the theoretical and experimental substantiation

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