SYNTHESIS OF 6-ALKYL-SUBSTITUTED DERIVATIVES OF 7,8-DIHYDROXY-4-METHYL-2-PHENYLBENZO[b]PYRILIUM PERCHLORATE
The development of new reagents based on benzopyrylium derivatives with enhanced chemical and analytical properties is of considerable interest, as their preparative synthesis is relatively straightforward and typically involves the condensation of triatomic phenols with β-dicarbonyl compounds. Benz...
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| Date: | 2025 |
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| Main Authors: | , , , , , |
| Format: | Article |
| Language: | English |
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V.I.Vernadsky Institute of General and Inorganic Chemistry
2025
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| Online Access: | https://ucj.org.ua/index.php/journal/article/view/758 |
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| Journal Title: | Ukrainian Chemistry Journal |
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Ukrainian Chemistry Journal| _version_ | 1859471888277831680 |
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| author | Barbalat, Dmytro Sazonov, Kyrylo Snihur, Kyrylo Guzenko, Olena Zhukovetska, Olena Snigur, Denys |
| author_facet | Barbalat, Dmytro Sazonov, Kyrylo Snihur, Kyrylo Guzenko, Olena Zhukovetska, Olena Snigur, Denys |
| author_sort | Barbalat, Dmytro |
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| collection | OJS |
| datestamp_date | 2026-03-09T13:19:22Z |
| description | The development of new reagents based on benzopyrylium derivatives with enhanced chemical and analytical properties is of considerable interest, as their preparative synthesis is relatively straightforward and typically involves the condensation of triatomic phenols with β-dicarbonyl compounds. Benzopyrylium derivatives are highly reactive species capable of undergoing redox processes, forming complexes with multivalent metal ions, and participating in acid–base transformations in solution. It is particularly noteworthy that hydroxy-substituted benzopyrylium derivatives can convert into anhydro bases with a quinoid structure upon complex formation. This transformation results in a pronounced bathochromic shift of the absorption band and significantly enhances the contrast and detectability of analytical reactions. This work is devoted to the development of a method for obtaining new 6-substituted derivatives of 7,8-dihydroxy-4-methyl-2-phenylbenzo[b]pyrylium perchlorate, which can be used as complexing reagents for the extraction-spectrophotometric determination of polyvalent metal ions, as well as to reduce the duration and complexity of the synthesis. An approach is proposed, which consists in the condensation of equimolar amounts of 4-alkyl derivatives of pyrogallol and benzoylacetone at boiling for 30–60 min in the presence of perchloric acid, and the formed crystalline products are suitable for use in spectrophotometric analysis and do not require additional complex purification, which leads to a reduction in the complexity and duration of the synthesis by 2–3 times. Seven new 6-substituted derivatives of 7,8-dihydroxy-4-methyl-2-phenylbenzo[b]pyrylium perchlorate were obtained, which were identified by IR, NMR, and mass spectrometry, and their purity and identity were proven by high-performance liquid chromatography. |
| first_indexed | 2026-03-12T15:49:41Z |
| format | Article |
| id | oai:ojs2.1444248.nisspano.web.hosting-test.net:article-758 |
| institution | Ukrainian Chemistry Journal |
| keywords_txt_mv | keywords |
| language | English |
| last_indexed | 2026-03-12T15:49:41Z |
| publishDate | 2025 |
| publisher | V.I.Vernadsky Institute of General and Inorganic Chemistry |
| record_format | ojs |
| spelling | oai:ojs2.1444248.nisspano.web.hosting-test.net:article-7582026-03-09T13:19:22Z SYNTHESIS OF 6-ALKYL-SUBSTITUTED DERIVATIVES OF 7,8-DIHYDROXY-4-METHYL-2-PHENYLBENZO[b]PYRILIUM PERCHLORATE Barbalat, Dmytro Sazonov, Kyrylo Snihur, Kyrylo Guzenko, Olena Zhukovetska, Olena Snigur, Denys 7,8-dihydroxybenzo[b]pyrylium derivatives, organic synthesis, organic analytical reagents, heterocyclic aromatic cations, benzopyrylium dyes. The development of new reagents based on benzopyrylium derivatives with enhanced chemical and analytical properties is of considerable interest, as their preparative synthesis is relatively straightforward and typically involves the condensation of triatomic phenols with β-dicarbonyl compounds. Benzopyrylium derivatives are highly reactive species capable of undergoing redox processes, forming complexes with multivalent metal ions, and participating in acid–base transformations in solution. It is particularly noteworthy that hydroxy-substituted benzopyrylium derivatives can convert into anhydro bases with a quinoid structure upon complex formation. This transformation results in a pronounced bathochromic shift of the absorption band and significantly enhances the contrast and detectability of analytical reactions. This work is devoted to the development of a method for obtaining new 6-substituted derivatives of 7,8-dihydroxy-4-methyl-2-phenylbenzo[b]pyrylium perchlorate, which can be used as complexing reagents for the extraction-spectrophotometric determination of polyvalent metal ions, as well as to reduce the duration and complexity of the synthesis. An approach is proposed, which consists in the condensation of equimolar amounts of 4-alkyl derivatives of pyrogallol and benzoylacetone at boiling for 30–60 min in the presence of perchloric acid, and the formed crystalline products are suitable for use in spectrophotometric analysis and do not require additional complex purification, which leads to a reduction in the complexity and duration of the synthesis by 2–3 times. Seven new 6-substituted derivatives of 7,8-dihydroxy-4-methyl-2-phenylbenzo[b]pyrylium perchlorate were obtained, which were identified by IR, NMR, and mass spectrometry, and their purity and identity were proven by high-performance liquid chromatography. V.I.Vernadsky Institute of General and Inorganic Chemistry 2025-12-25 Article Article Organic chemistry Органическая xимия Органічна xімія application/pdf https://ucj.org.ua/index.php/journal/article/view/758 10.33609/2708-129X.91.11.2025.63-70 Ukrainian Chemistry Journal; Vol. 91 No. 11 (2025): Ukrainian Chemistry Journal; 63-70 Украинский химический журнал; Том 91 № 11 (2025): Ukrainian Chemistry Journal; 63-70 Український хімічний журнал; Том 91 № 11 (2025): Ukrainian Chemistry Journal; 63-70 2708-129X 2708-1281 en https://ucj.org.ua/index.php/journal/article/view/758/393 |
| spellingShingle | Barbalat, Dmytro Sazonov, Kyrylo Snihur, Kyrylo Guzenko, Olena Zhukovetska, Olena Snigur, Denys SYNTHESIS OF 6-ALKYL-SUBSTITUTED DERIVATIVES OF 7,8-DIHYDROXY-4-METHYL-2-PHENYLBENZO[b]PYRILIUM PERCHLORATE |
| title | SYNTHESIS OF 6-ALKYL-SUBSTITUTED DERIVATIVES OF 7,8-DIHYDROXY-4-METHYL-2-PHENYLBENZO[b]PYRILIUM PERCHLORATE |
| title_full | SYNTHESIS OF 6-ALKYL-SUBSTITUTED DERIVATIVES OF 7,8-DIHYDROXY-4-METHYL-2-PHENYLBENZO[b]PYRILIUM PERCHLORATE |
| title_fullStr | SYNTHESIS OF 6-ALKYL-SUBSTITUTED DERIVATIVES OF 7,8-DIHYDROXY-4-METHYL-2-PHENYLBENZO[b]PYRILIUM PERCHLORATE |
| title_full_unstemmed | SYNTHESIS OF 6-ALKYL-SUBSTITUTED DERIVATIVES OF 7,8-DIHYDROXY-4-METHYL-2-PHENYLBENZO[b]PYRILIUM PERCHLORATE |
| title_short | SYNTHESIS OF 6-ALKYL-SUBSTITUTED DERIVATIVES OF 7,8-DIHYDROXY-4-METHYL-2-PHENYLBENZO[b]PYRILIUM PERCHLORATE |
| title_sort | synthesis of 6-alkyl-substituted derivatives of 7,8-dihydroxy-4-methyl-2-phenylbenzo[b]pyrilium perchlorate |
| topic_facet | 7,8-dihydroxybenzo[b]pyrylium derivatives organic synthesis organic analytical reagents heterocyclic aromatic cations benzopyrylium dyes. |
| url | https://ucj.org.ua/index.php/journal/article/view/758 |
| work_keys_str_mv | AT barbalatdmytro synthesisof6alkylsubstitutedderivativesof78dihydroxy4methyl2phenylbenzobpyriliumperchlorate AT sazonovkyrylo synthesisof6alkylsubstitutedderivativesof78dihydroxy4methyl2phenylbenzobpyriliumperchlorate AT snihurkyrylo synthesisof6alkylsubstitutedderivativesof78dihydroxy4methyl2phenylbenzobpyriliumperchlorate AT guzenkoolena synthesisof6alkylsubstitutedderivativesof78dihydroxy4methyl2phenylbenzobpyriliumperchlorate AT zhukovetskaolena synthesisof6alkylsubstitutedderivativesof78dihydroxy4methyl2phenylbenzobpyriliumperchlorate AT snigurdenys synthesisof6alkylsubstitutedderivativesof78dihydroxy4methyl2phenylbenzobpyriliumperchlorate |