Twice as Nice: The Duff Formylation of Umbelliferone Revised
More efficient and preferably more convenient and greener synthetic solutions in coumarin scaffold functionalization are in steady demand. The Duff <i>ortho</i>-formylation of unsubstituted umbelliferone was revised in this study. The reaction conditions were optimized based upon data fr...
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| Format: | Article |
| Language: | English |
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MDPI AG
2021-12-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/26/24/7482 |
| _version_ | 1827670856013185024 |
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| author | Vladislav V. Skarga Vadim V. Negrebetsky Yuri I. Baukov Mikhail V. Malakhov |
| author_facet | Vladislav V. Skarga Vadim V. Negrebetsky Yuri I. Baukov Mikhail V. Malakhov |
| author_sort | Vladislav V. Skarga |
| collection | DOAJ |
| description | More efficient and preferably more convenient and greener synthetic solutions in coumarin scaffold functionalization are in steady demand. The Duff <i>ortho</i>-formylation of unsubstituted umbelliferone was revised in this study. The reaction conditions were optimized based upon data from the literature analysis and resulted in unexpectedly rapid <i>ortho</i>-formylation of umbelliferone, yielding a mixture of <i>ortho</i>-formyl position isomers. Thorough studies on the separation of <i>ortho</i>-formylated umbelliferones using chromatographic and recrystallization methods as well as the evaluation of their solubility in common organic solvents led to complete resolution of 8-formyl- and 6-formylumbelliferones. The precise protocol for simultaneous preparation, extraction, and purification of 8-formyl- and 6-formylumbelliferones is provided, and the prospective studies of biological and pharmacological activities of these compounds are synopsized. |
| first_indexed | 2024-03-10T03:28:55Z |
| format | Article |
| id | doaj.art-0b47a2eb722e41e6b7835a30443189a0 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T03:28:55Z |
| publishDate | 2021-12-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-0b47a2eb722e41e6b7835a30443189a02023-11-23T09:44:46ZengMDPI AGMolecules1420-30492021-12-012624748210.3390/molecules26247482Twice as Nice: The Duff Formylation of Umbelliferone RevisedVladislav V. Skarga0Vadim V. Negrebetsky1Yuri I. Baukov2Mikhail V. Malakhov3Institute of Translational Medicine, Pirogov Russian National Research Medical University, 117997 Moscow, RussiaInstitute of Translational Medicine, Pirogov Russian National Research Medical University, 117997 Moscow, RussiaInstitute of Translational Medicine, Pirogov Russian National Research Medical University, 117997 Moscow, RussiaInstitute of Translational Medicine, Pirogov Russian National Research Medical University, 117997 Moscow, RussiaMore efficient and preferably more convenient and greener synthetic solutions in coumarin scaffold functionalization are in steady demand. The Duff <i>ortho</i>-formylation of unsubstituted umbelliferone was revised in this study. The reaction conditions were optimized based upon data from the literature analysis and resulted in unexpectedly rapid <i>ortho</i>-formylation of umbelliferone, yielding a mixture of <i>ortho</i>-formyl position isomers. Thorough studies on the separation of <i>ortho</i>-formylated umbelliferones using chromatographic and recrystallization methods as well as the evaluation of their solubility in common organic solvents led to complete resolution of 8-formyl- and 6-formylumbelliferones. The precise protocol for simultaneous preparation, extraction, and purification of 8-formyl- and 6-formylumbelliferones is provided, and the prospective studies of biological and pharmacological activities of these compounds are synopsized.https://www.mdpi.com/1420-3049/26/24/7482formylationthe Duff reactioncoumarinsumbelliferones8-formylumbelliferone6-formylumbelliferone |
| spellingShingle | Vladislav V. Skarga Vadim V. Negrebetsky Yuri I. Baukov Mikhail V. Malakhov Twice as Nice: The Duff Formylation of Umbelliferone Revised Molecules formylation the Duff reaction coumarins umbelliferones 8-formylumbelliferone 6-formylumbelliferone |
| title | Twice as Nice: The Duff Formylation of Umbelliferone Revised |
| title_full | Twice as Nice: The Duff Formylation of Umbelliferone Revised |
| title_fullStr | Twice as Nice: The Duff Formylation of Umbelliferone Revised |
| title_full_unstemmed | Twice as Nice: The Duff Formylation of Umbelliferone Revised |
| title_short | Twice as Nice: The Duff Formylation of Umbelliferone Revised |
| title_sort | twice as nice the duff formylation of umbelliferone revised |
| topic | formylation the Duff reaction coumarins umbelliferones 8-formylumbelliferone 6-formylumbelliferone |
| url | https://www.mdpi.com/1420-3049/26/24/7482 |
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