Trifluoroacetic Acid-Mediated Oxidative Self-Condensation of Acetophenones in the Presence of SeO(2): A Serendipitous Approach for the Synthesis of Fused [1,3]Dioxolo[4,5-d][1,3]dioxoles

[Image: see text] A method for the synthesis of fused 1,3-dioxolanes was developed by self-condensation of glyoxal generated in situ by oxidation of acetophenones with SeO(2) in the presence of trifluoroacetic acid. Three molecules of the glyoxal generated by oxidation of ketone with SeO(2) condense...

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Autores principales: Marpna, Ibakyntiew D., Shangpliang, O. Risuklang, Wanniang, Kmendashisha, Kshiar, Baskhemlang, Lipon, Tyrchain Mitre, Laloo, Badaker M., Myrboh, Bekington
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2021
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8190894/
https://www.ncbi.nlm.nih.gov/pubmed/34124474
http://dx.doi.org/10.1021/acsomega.1c01466
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author Marpna, Ibakyntiew D.
Shangpliang, O. Risuklang
Wanniang, Kmendashisha
Kshiar, Baskhemlang
Lipon, Tyrchain Mitre
Laloo, Badaker M.
Myrboh, Bekington
author_facet Marpna, Ibakyntiew D.
Shangpliang, O. Risuklang
Wanniang, Kmendashisha
Kshiar, Baskhemlang
Lipon, Tyrchain Mitre
Laloo, Badaker M.
Myrboh, Bekington
author_sort Marpna, Ibakyntiew D.
collection PubMed
description [Image: see text] A method for the synthesis of fused 1,3-dioxolanes was developed by self-condensation of glyoxal generated in situ by oxidation of acetophenones with SeO(2) in the presence of trifluoroacetic acid. Three molecules of the glyoxal generated by oxidation of ketone with SeO(2) condensed to form architecturally novel oxygen-containing heterocycles (3a-aryldihydro-[1,3]dioxolo[4,5-d][1,3] dioxole-2,5-diyl)bis(phenylmethanones). This reaction provides a unique methodology for the construction of four C–O bonds in a concerted fashion, generating highly embedded oxygen heterocycles from readily available ketones using affordable shelf reagents and simple reaction conditions.
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spelling pubmed-81908942021-06-11 Trifluoroacetic Acid-Mediated Oxidative Self-Condensation of Acetophenones in the Presence of SeO(2): A Serendipitous Approach for the Synthesis of Fused [1,3]Dioxolo[4,5-d][1,3]dioxoles Marpna, Ibakyntiew D. Shangpliang, O. Risuklang Wanniang, Kmendashisha Kshiar, Baskhemlang Lipon, Tyrchain Mitre Laloo, Badaker M. Myrboh, Bekington ACS Omega [Image: see text] A method for the synthesis of fused 1,3-dioxolanes was developed by self-condensation of glyoxal generated in situ by oxidation of acetophenones with SeO(2) in the presence of trifluoroacetic acid. Three molecules of the glyoxal generated by oxidation of ketone with SeO(2) condensed to form architecturally novel oxygen-containing heterocycles (3a-aryldihydro-[1,3]dioxolo[4,5-d][1,3] dioxole-2,5-diyl)bis(phenylmethanones). This reaction provides a unique methodology for the construction of four C–O bonds in a concerted fashion, generating highly embedded oxygen heterocycles from readily available ketones using affordable shelf reagents and simple reaction conditions. American Chemical Society 2021-05-28 /pmc/articles/PMC8190894/ /pubmed/34124474 http://dx.doi.org/10.1021/acsomega.1c01466 Text en © 2021 The Authors. Published by American Chemical Society Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works (https://creativecommons.org/licenses/by-nc-nd/4.0/).
spellingShingle Marpna, Ibakyntiew D.
Shangpliang, O. Risuklang
Wanniang, Kmendashisha
Kshiar, Baskhemlang
Lipon, Tyrchain Mitre
Laloo, Badaker M.
Myrboh, Bekington
Trifluoroacetic Acid-Mediated Oxidative Self-Condensation of Acetophenones in the Presence of SeO(2): A Serendipitous Approach for the Synthesis of Fused [1,3]Dioxolo[4,5-d][1,3]dioxoles
title Trifluoroacetic Acid-Mediated Oxidative Self-Condensation of Acetophenones in the Presence of SeO(2): A Serendipitous Approach for the Synthesis of Fused [1,3]Dioxolo[4,5-d][1,3]dioxoles
title_full Trifluoroacetic Acid-Mediated Oxidative Self-Condensation of Acetophenones in the Presence of SeO(2): A Serendipitous Approach for the Synthesis of Fused [1,3]Dioxolo[4,5-d][1,3]dioxoles
title_fullStr Trifluoroacetic Acid-Mediated Oxidative Self-Condensation of Acetophenones in the Presence of SeO(2): A Serendipitous Approach for the Synthesis of Fused [1,3]Dioxolo[4,5-d][1,3]dioxoles
title_full_unstemmed Trifluoroacetic Acid-Mediated Oxidative Self-Condensation of Acetophenones in the Presence of SeO(2): A Serendipitous Approach for the Synthesis of Fused [1,3]Dioxolo[4,5-d][1,3]dioxoles
title_short Trifluoroacetic Acid-Mediated Oxidative Self-Condensation of Acetophenones in the Presence of SeO(2): A Serendipitous Approach for the Synthesis of Fused [1,3]Dioxolo[4,5-d][1,3]dioxoles
title_sort trifluoroacetic acid-mediated oxidative self-condensation of acetophenones in the presence of seo(2): a serendipitous approach for the synthesis of fused [1,3]dioxolo[4,5-d][1,3]dioxoles
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8190894/
https://www.ncbi.nlm.nih.gov/pubmed/34124474
http://dx.doi.org/10.1021/acsomega.1c01466
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