Stabilizing Influence of Electron-Deficient Triazole Fragment on the Furan Heterocycle in Renewable Platform Chemicals

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Resumo

The effect of an aromatic triazole ring conjugated with a furan heterocycle on the stability of furan under various reaction conditions was studied, and a significant reduction in the degree of degradation of the electron-rich furan core and hydrolysis of the ester group under the action of a model acid and base in various organic solvents was shown. The lowest degree of degradation and hydrolysis of the triazole-substituted 2-furoic acid ester was achieved in dioxane, as well as in polar aprotic solvents (DMSO and DMF). It was shown that under the same conditions, a significant tarring and hydrolysis of the furan ester, which does not contain a conjugated triazole fragment, occurs.

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Sobre autores

D. Kolykhalov

Tula State University

Email: karbo@ioc.ac.ru
Rússia, 300012 Tula

A. Golysheva

Tula State University

Email: karbo@ioc.ac.ru
Rússia, 300012 Tula

B. Karlinskii

Tula State University; N.D. Zelinsky Institute of Organic Chemistry of Russian Academy of Sciences

Autor responsável pela correspondência
Email: karbo@ioc.ac.ru
Rússia, 300012 Tula; 119991 Moscow

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2. Fig. 1. Scheme of synthesis of triazolyl-substituted furan derivative of T-MPEK.

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3. Fig. 2. Photographs of reaction systems before heating (top) and after completion of the stability study experiment (bottom).

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4. Fig. 3. Morphology of the solid precipitate obtained during treatment of MEPC solution in acetonitrile with sulfuric acid.

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5. Fig. 4. IR spectra of MEPC (1) and precipitates obtained after treatment of MEPC solution with 1 equiv. H2SO4 in acetonitrile (2) and 1 equiv. NaOH in 1,4-dioxane (3).

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6. Fig. 5. Morphology of precipitates obtained during treatment of T-MEPC solution in DMF with sulfuric acid (a) and MEPC solution in dioxane with sodium hydroxide (b).

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7. Fig. 6. IR spectra of T-MEPC (1) and the precipitate obtained after treating the T-MEPC solution in DMF with sulfuric acid (2).

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8. Fig. 7. Graphic map of the stability of MEPC and T-MEPC under various reaction conditions. The color of the circle corresponds to the degree of conversion of the studied compound during hydrolysis or destruction under these reaction conditions.

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