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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ftdoajarticles:oai:doaj.org/article:8552844a44a04e29b0f3e203b4bd7ed2 2023-07-23T04:18:48+02:00 Fe-Catalyzed Synthesis of 2-Benzoxazolone—An Important Fragment of Biologically Active Compounds Zemfira G. Urazbaeva Alfiya R. Bayguzina Ilfir R. Ramazanov 2022-11-01T00:00:00Z https://doi.org/10.3390/ecsoc-26-13564 https://doaj.org/article/8552844a44a04e29b0f3e203b4bd7ed2 EN eng MDPI AG https://www.mdpi.com/2673-4583/12/1/63 https://doaj.org/toc/2673-4583 doi:10.3390/ecsoc-26-13564 2673-4583 https://doaj.org/article/8552844a44a04e29b0f3e203b4bd7ed2 Chemistry Proceedings, Vol 12, Iss 63, p 63 (2022) 2-benzoxazolone oxazolidin-2-one iron catalysis heterocyclization oxidative carbonylation Chemistry QD1-999 article 2022 ftdoajarticles https://doi.org/10.3390/ecsoc-26-13564 2023-07-02T00:38:41Z 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 FeCl 3 *6H 2 O and Fe(acac) 3 as catalysts under relatively mild conditions (100–120 °C) in the presence of CCl 4 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. Article in Journal/Newspaper Carbonic acid Directory of Open Access Journals: DOAJ Articles The 26th International Electronic Conference on Synthetic Organic Chemistry 63 |
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Open Polar |
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Directory of Open Access Journals: DOAJ Articles |
op_collection_id |
ftdoajarticles |
language |
English |
topic |
2-benzoxazolone oxazolidin-2-one iron catalysis heterocyclization oxidative carbonylation Chemistry QD1-999 |
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2-benzoxazolone oxazolidin-2-one iron catalysis heterocyclization oxidative carbonylation Chemistry QD1-999 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 Chemistry QD1-999 |
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 FeCl 3 *6H 2 O and Fe(acac) 3 as catalysts under relatively mild conditions (100–120 °C) in the presence of CCl 4 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 |
Article in Journal/Newspaper |
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 |
MDPI AG |
publishDate |
2022 |
url |
https://doi.org/10.3390/ecsoc-26-13564 https://doaj.org/article/8552844a44a04e29b0f3e203b4bd7ed2 |
genre |
Carbonic acid |
genre_facet |
Carbonic acid |
op_source |
Chemistry Proceedings, Vol 12, Iss 63, p 63 (2022) |
op_relation |
https://www.mdpi.com/2673-4583/12/1/63 https://doaj.org/toc/2673-4583 doi:10.3390/ecsoc-26-13564 2673-4583 https://doaj.org/article/8552844a44a04e29b0f3e203b4bd7ed2 |
op_doi |
https://doi.org/10.3390/ecsoc-26-13564 |
container_title |
The 26th International Electronic Conference on Synthetic Organic Chemistry |
container_start_page |
63 |
_version_ |
1772181418163568640 |