СИНТЕЗ ТА ВЛАСТИВОСТІ ХАЛКОНІВ НА ОСНОВІ ДЕГІДРАЦЕТОВОЇ КИСЛОТИ
The Knoevenagel condensation reaction between dehydracetic acid and aromatic aldehydes is described in this work. The reaction is carried out directly between dehydroacetic acid and aromatic aldehydes in the presence of organic bases. The optimal conditions for the Knoevenagel reaction based on dehy...
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| Дата: | 2021 |
|---|---|
| Автори: | , , , , , , , , |
| Формат: | Стаття |
| Мова: | English |
| Опубліковано: |
V.I.Vernadsky Institute of General and Inorganic Chemistry
2021
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| Онлайн доступ: | https://ucj.org.ua/index.php/journal/article/view/309 |
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| Назва журналу: | Ukrainian Chemistry Journal |
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oai:ojs2.1444248.nisspano.web.hosting-test.net:article-3092021-08-02T08:57:29Z SYNTHESIS AND PROPERTIES OF CHALCONES BASED ON DEHYDROACETIC ACID СИНТЕЗ ТА ВЛАСТИВОСТІ ХАЛКОНІВ НА ОСНОВІ ДЕГІДРАЦЕТОВОЇ КИСЛОТИ Tretyakova, Iryna Chernii, Viktor Fedosova, Natalia Denisenko, Iryna Dovbii, Yan Kovalska, Vladyslava Chernii, Svitlana Pekhnyo, Vasyl Starukhin, Alexandr dehydroacetic acid, Knoevenagel condensation, chalcones. The Knoevenagel condensation reaction between dehydracetic acid and aromatic aldehydes is described in this work. The reaction is carried out directly between dehydroacetic acid and aromatic aldehydes in the presence of organic bases. The optimal conditions for the Knoevenagel reaction based on dehydroacetic acid and various aldehydes were determined. Twenty-one chalcones with substituents of different nature were synthesized. The composition and structure of the obtained compounds were determined. All characteristic signals of chalcones are present in the 1H NMR spectra of the obtained compounds registered in CDCl3 and DMSO-d6: OH groups in the range of 18.7–16.5 ppm, CH proton – 6.3–5.9 ppm, and methyl group of the pyran cycle 2.3–2.2 ppm. The corresponding signals of methine protons and aryl substituents are also present in the spectra. The most sensitive to solvent changes is the OH proton bound by an intramolecular hydrogen bond to the carbonyl group of the pyran ring. Signals in DMSO are usually shifted by 0.1–1.0 ppm in a stronger field compared to CDCl3 for dehydroacetic acid and chalcones based on it. CH proton signals are shifted by approximately 0.3 ppm in a weaker field, and the signals of the protons of the methyl group are almost insensitive to the solvent. The optical properties of obtained compounds were investigated in DMF, MeOH, MeCN. The synthesized chalcones absorb light in the visible range 330–490 nm with molar extinction coefficients of 3.5–4.5. The solvatochromic effects for most of them are weak – the position of the maximum changes by less than 10 nm. The electron-donor substituents in the phenyl ring (-NMe2 and -NEt2) shift the absorption maximum bathochromically by almost 100 nm compared to others in all investigated solvents. V.I.Vernadsky Institute of General and Inorganic Chemistry 2021-06-25 Article Article Inorganic Chemistry Неорганическая химия Неорганічна хімія application/pdf https://ucj.org.ua/index.php/journal/article/view/309 10.33609/2708-129X.87.05.2021.3-14 Ukrainian Chemistry Journal; Vol. 87 No. 5 (2021): Ukrainian Chemistry Journal; 3-14 Украинский химический журнал; Том 87 № 5 (2021): Ukrainian Chemistry Journal; 3-14 Український хімічний журнал; Том 87 № 5 (2021): Український хімічний журнал; 3-14 2708-129X 2708-1281 en https://ucj.org.ua/index.php/journal/article/view/309/168 |
| institution |
Ukrainian Chemistry Journal |
| baseUrl_str |
|
| datestamp_date |
2021-08-02T08:57:29Z |
| collection |
OJS |
| language |
English |
| topic_facet |
dehydroacetic acid Knoevenagel condensation chalcones. |
| format |
Article |
| author |
Tretyakova, Iryna Chernii, Viktor Fedosova, Natalia Denisenko, Iryna Dovbii, Yan Kovalska, Vladyslava Chernii, Svitlana Pekhnyo, Vasyl Starukhin, Alexandr |
| spellingShingle |
Tretyakova, Iryna Chernii, Viktor Fedosova, Natalia Denisenko, Iryna Dovbii, Yan Kovalska, Vladyslava Chernii, Svitlana Pekhnyo, Vasyl Starukhin, Alexandr СИНТЕЗ ТА ВЛАСТИВОСТІ ХАЛКОНІВ НА ОСНОВІ ДЕГІДРАЦЕТОВОЇ КИСЛОТИ |
| author_facet |
Tretyakova, Iryna Chernii, Viktor Fedosova, Natalia Denisenko, Iryna Dovbii, Yan Kovalska, Vladyslava Chernii, Svitlana Pekhnyo, Vasyl Starukhin, Alexandr |
| author_sort |
Tretyakova, Iryna |
| title |
СИНТЕЗ ТА ВЛАСТИВОСТІ ХАЛКОНІВ НА ОСНОВІ ДЕГІДРАЦЕТОВОЇ КИСЛОТИ |
| title_short |
СИНТЕЗ ТА ВЛАСТИВОСТІ ХАЛКОНІВ НА ОСНОВІ ДЕГІДРАЦЕТОВОЇ КИСЛОТИ |
| title_full |
СИНТЕЗ ТА ВЛАСТИВОСТІ ХАЛКОНІВ НА ОСНОВІ ДЕГІДРАЦЕТОВОЇ КИСЛОТИ |
| title_fullStr |
СИНТЕЗ ТА ВЛАСТИВОСТІ ХАЛКОНІВ НА ОСНОВІ ДЕГІДРАЦЕТОВОЇ КИСЛОТИ |
| title_full_unstemmed |
СИНТЕЗ ТА ВЛАСТИВОСТІ ХАЛКОНІВ НА ОСНОВІ ДЕГІДРАЦЕТОВОЇ КИСЛОТИ |
| title_sort |
синтез та властивості халконів на основі дегідрацетової кислоти |
| title_alt |
SYNTHESIS AND PROPERTIES OF CHALCONES BASED ON DEHYDROACETIC ACID |
| description |
The Knoevenagel condensation reaction between dehydracetic acid and aromatic aldehydes is described in this work. The reaction is carried out directly between dehydroacetic acid and aromatic aldehydes in the presence of organic bases. The optimal conditions for the Knoevenagel reaction based on dehydroacetic acid and various aldehydes were determined. Twenty-one chalcones with substituents of different nature were synthesized. The composition and structure of the obtained compounds were determined. All characteristic signals of chalcones are present in the 1H NMR spectra of the obtained compounds registered in CDCl3 and DMSO-d6: OH groups in the range of 18.7–16.5 ppm, CH proton – 6.3–5.9 ppm, and methyl group of the pyran cycle 2.3–2.2 ppm. The corresponding signals of methine protons and aryl substituents are also present in the spectra. The most sensitive to solvent changes is the OH proton bound by an intramolecular hydrogen bond to the carbonyl group of the pyran ring. Signals in DMSO are usually shifted by 0.1–1.0 ppm in a stronger field compared to CDCl3 for dehydroacetic acid and chalcones based on it. CH proton signals are shifted by approximately 0.3 ppm in a weaker field, and the signals of the protons of the methyl group are almost insensitive to the solvent. The optical properties of obtained compounds were investigated in DMF, MeOH, MeCN. The synthesized chalcones absorb light in the visible range 330–490 nm with molar extinction coefficients of 3.5–4.5. The solvatochromic effects for most of them are weak – the position of the maximum changes by less than 10 nm. The electron-donor substituents in the phenyl ring (-NMe2 and -NEt2) shift the absorption maximum bathochromically by almost 100 nm compared to others in all investigated solvents. |
| publisher |
V.I.Vernadsky Institute of General and Inorganic Chemistry |
| publishDate |
2021 |
| url |
https://ucj.org.ua/index.php/journal/article/view/309 |
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