Fe-Catalyzed Synthesis of 2-Benzoxazolone—An Important Fragment of Biologically Active Compounds
2-Benzoxazolone, as well as its derivatives, are valuable structural fragments of a number of important biologically active substances. 2-Benzoxazolone derivatives are promising as antitumor, antimicrobial, antiretroviral, anticonvulsant, tranquilizing, and insecticidal agents. 2-Benzoxazolone is us...
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ftmdpi:oai:mdpi.com:/2673-4583/12/1/63/ 2023-08-20T04:05:53+02:00 Fe-Catalyzed Synthesis of 2-Benzoxazolone—An Important Fragment of Biologically Active Compounds Zemfira G. Urazbaeva Alfiya R. Bayguzina Ilfir R. Ramazanov 2022-11-14 application/pdf https://doi.org/10.3390/ecsoc-26-13564 EN eng Multidisciplinary Digital Publishing Institute https://dx.doi.org/10.3390/ecsoc-26-13564 https://creativecommons.org/licenses/by/4.0/ Chemistry Proceedings; Volume 12; Issue 1; Pages: 63 2-benzoxazolone oxazolidin-2-one iron catalysis heterocyclization oxidative carbonylation Text 2022 ftmdpi https://doi.org/10.3390/ecsoc-26-13564 2023-08-01T08:36:36Z 2-Benzoxazolone, as well as its derivatives, are valuable structural fragments of a number of important biologically active substances. 2-Benzoxazolone derivatives are promising as antitumor, antimicrobial, antiretroviral, anticonvulsant, tranquilizing, and insecticidal agents. 2-Benzoxazolone is usually produced by the condensation of o-aminophenol with urea, phosgene, and other carbonic acid derivatives. There are also methods for the synthesis of 2-benzoxazolone from salicylamide with trichloroisocyanuric acid as a chlorinating agent, from hydroxybenzoic acid using ammonium azide and the Vilsmeier complex. The disadvantages of these methods are the high cost of the initial reagents, the need to use aggressive and toxic reagents (phosgene, ammonium azide), and the complexity of the hardware design for the reactors. We have developed the highly efficient oxidative cyclocarbonylation of 2-aminophenol to oxazolidin-2-one using FeCl3*6H2O and Fe(acac)3 as catalysts under relatively mild conditions (100–120 °C) in the presence of CCl4 and water. We assume that in situ-formed carbon dioxide is involved in a cyclization reaction with o-aminophenol to form the target 2-benzoxazole. The reaction takes 2–10 h to give 2-benzoxazolone a high yield. Text Carbonic acid MDPI Open Access Publishing The 26th International Electronic Conference on Synthetic Organic Chemistry 63 |
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MDPI Open Access Publishing |
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English |
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2-benzoxazolone oxazolidin-2-one iron catalysis heterocyclization oxidative carbonylation |
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2-benzoxazolone oxazolidin-2-one iron catalysis heterocyclization oxidative carbonylation Zemfira G. Urazbaeva Alfiya R. Bayguzina Ilfir R. Ramazanov Fe-Catalyzed Synthesis of 2-Benzoxazolone—An Important Fragment of Biologically Active Compounds |
topic_facet |
2-benzoxazolone oxazolidin-2-one iron catalysis heterocyclization oxidative carbonylation |
description |
2-Benzoxazolone, as well as its derivatives, are valuable structural fragments of a number of important biologically active substances. 2-Benzoxazolone derivatives are promising as antitumor, antimicrobial, antiretroviral, anticonvulsant, tranquilizing, and insecticidal agents. 2-Benzoxazolone is usually produced by the condensation of o-aminophenol with urea, phosgene, and other carbonic acid derivatives. There are also methods for the synthesis of 2-benzoxazolone from salicylamide with trichloroisocyanuric acid as a chlorinating agent, from hydroxybenzoic acid using ammonium azide and the Vilsmeier complex. The disadvantages of these methods are the high cost of the initial reagents, the need to use aggressive and toxic reagents (phosgene, ammonium azide), and the complexity of the hardware design for the reactors. We have developed the highly efficient oxidative cyclocarbonylation of 2-aminophenol to oxazolidin-2-one using FeCl3*6H2O and Fe(acac)3 as catalysts under relatively mild conditions (100–120 °C) in the presence of CCl4 and water. We assume that in situ-formed carbon dioxide is involved in a cyclization reaction with o-aminophenol to form the target 2-benzoxazole. The reaction takes 2–10 h to give 2-benzoxazolone a high yield. |
format |
Text |
author |
Zemfira G. Urazbaeva Alfiya R. Bayguzina Ilfir R. Ramazanov |
author_facet |
Zemfira G. Urazbaeva Alfiya R. Bayguzina Ilfir R. Ramazanov |
author_sort |
Zemfira G. Urazbaeva |
title |
Fe-Catalyzed Synthesis of 2-Benzoxazolone—An Important Fragment of Biologically Active Compounds |
title_short |
Fe-Catalyzed Synthesis of 2-Benzoxazolone—An Important Fragment of Biologically Active Compounds |
title_full |
Fe-Catalyzed Synthesis of 2-Benzoxazolone—An Important Fragment of Biologically Active Compounds |
title_fullStr |
Fe-Catalyzed Synthesis of 2-Benzoxazolone—An Important Fragment of Biologically Active Compounds |
title_full_unstemmed |
Fe-Catalyzed Synthesis of 2-Benzoxazolone—An Important Fragment of Biologically Active Compounds |
title_sort |
fe-catalyzed synthesis of 2-benzoxazolone—an important fragment of biologically active compounds |
publisher |
Multidisciplinary Digital Publishing Institute |
publishDate |
2022 |
url |
https://doi.org/10.3390/ecsoc-26-13564 |
genre |
Carbonic acid |
genre_facet |
Carbonic acid |
op_source |
Chemistry Proceedings; Volume 12; Issue 1; Pages: 63 |
op_relation |
https://dx.doi.org/10.3390/ecsoc-26-13564 |
op_rights |
https://creativecommons.org/licenses/by/4.0/ |
op_doi |
https://doi.org/10.3390/ecsoc-26-13564 |
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The 26th International Electronic Conference on Synthetic Organic Chemistry |
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63 |
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1774716630344925184 |