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First synthesis of acylated nitrocyclopropanes

Although nitrocyclopropanedicarboxylic acid esters are widely used in organic syntheses, nitrocyclopropanes with an acyl group have not yet been synthesized. When adducts of β-nitrostyrene and 1,3-dicarbonyl compounds are treated with (diacetoxyiodo)benzene and tetrabutylammonium iodide, iodination...

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Autores principales: Iwai, Kento, Kamidate, Rikiya, Wada, Khimiya, Asahara, Haruyasu, Nishiwaki, Nagatoshi
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2023
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10291240/
https://www.ncbi.nlm.nih.gov/pubmed/37377773
http://dx.doi.org/10.3762/bjoc.19.67
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author Iwai, Kento
Kamidate, Rikiya
Wada, Khimiya
Asahara, Haruyasu
Nishiwaki, Nagatoshi
author_facet Iwai, Kento
Kamidate, Rikiya
Wada, Khimiya
Asahara, Haruyasu
Nishiwaki, Nagatoshi
author_sort Iwai, Kento
collection PubMed
description Although nitrocyclopropanedicarboxylic acid esters are widely used in organic syntheses, nitrocyclopropanes with an acyl group have not yet been synthesized. When adducts of β-nitrostyrene and 1,3-dicarbonyl compounds are treated with (diacetoxyiodo)benzene and tetrabutylammonium iodide, iodination occurs at the α-position of the nitro group, and the subsequent O-attack of the enol moiety leads to 2,3-dihydrofuran. Cyclopropane was successfully synthesized through C-attack as the acyl group became bulkier. The obtained nitrocyclopropane was transformed into furan upon treatment with tin(II) chloride via a ring-opening/ring-closure process.
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spelling pubmed-102912402023-06-27 First synthesis of acylated nitrocyclopropanes Iwai, Kento Kamidate, Rikiya Wada, Khimiya Asahara, Haruyasu Nishiwaki, Nagatoshi Beilstein J Org Chem Full Research Paper Although nitrocyclopropanedicarboxylic acid esters are widely used in organic syntheses, nitrocyclopropanes with an acyl group have not yet been synthesized. When adducts of β-nitrostyrene and 1,3-dicarbonyl compounds are treated with (diacetoxyiodo)benzene and tetrabutylammonium iodide, iodination occurs at the α-position of the nitro group, and the subsequent O-attack of the enol moiety leads to 2,3-dihydrofuran. Cyclopropane was successfully synthesized through C-attack as the acyl group became bulkier. The obtained nitrocyclopropane was transformed into furan upon treatment with tin(II) chloride via a ring-opening/ring-closure process. Beilstein-Institut 2023-06-21 /pmc/articles/PMC10291240/ /pubmed/37377773 http://dx.doi.org/10.3762/bjoc.19.67 Text en Copyright © 2023, Iwai et al. https://creativecommons.org/licenses/by/4.0/This is an open access article licensed under the terms of the Beilstein-Institut Open Access License Agreement (https://www.beilstein-journals.org/bjoc/terms/terms), which is identical to the Creative Commons Attribution 4.0 International License (https://creativecommons.org/licenses/by/4.0 (https://creativecommons.org/licenses/by/4.0/) ). The reuse of material under this license requires that the author(s), source and license are credited. Third-party material in this article could be subject to other licenses (typically indicated in the credit line), and in this case, users are required to obtain permission from the license holder to reuse the material.
spellingShingle Full Research Paper
Iwai, Kento
Kamidate, Rikiya
Wada, Khimiya
Asahara, Haruyasu
Nishiwaki, Nagatoshi
First synthesis of acylated nitrocyclopropanes
title First synthesis of acylated nitrocyclopropanes
title_full First synthesis of acylated nitrocyclopropanes
title_fullStr First synthesis of acylated nitrocyclopropanes
title_full_unstemmed First synthesis of acylated nitrocyclopropanes
title_short First synthesis of acylated nitrocyclopropanes
title_sort first synthesis of acylated nitrocyclopropanes
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10291240/
https://www.ncbi.nlm.nih.gov/pubmed/37377773
http://dx.doi.org/10.3762/bjoc.19.67
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