A Novel Method to Construct 2-Aminobenzofurans via [4 + 1] Cycloaddition Reaction of In Situ Generated Ortho-Quinone Methides with Isocyanides

A new approach for the synthesis of 2-aminobenzofurans has been described via Sc(OTf)(3) mediated formal cycloaddition of isocyanides with the in situ generated ortho-quinone methides (o-QMs) from o-hydroxybenzhydryl alcohol. Notably, as a class of readily available and highly active intermediates,...

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Autores principales: Lin, Huaxin, Tang, Senling, Pan, Yang, Liang, Peng, Ma, Xiaofeng, Jiao, Wei, Shao, Huawu
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
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Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9737762/
https://www.ncbi.nlm.nih.gov/pubmed/36500630
http://dx.doi.org/10.3390/molecules27238538
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author Lin, Huaxin
Tang, Senling
Pan, Yang
Liang, Peng
Ma, Xiaofeng
Jiao, Wei
Shao, Huawu
author_facet Lin, Huaxin
Tang, Senling
Pan, Yang
Liang, Peng
Ma, Xiaofeng
Jiao, Wei
Shao, Huawu
author_sort Lin, Huaxin
collection PubMed
description A new approach for the synthesis of 2-aminobenzofurans has been described via Sc(OTf)(3) mediated formal cycloaddition of isocyanides with the in situ generated ortho-quinone methides (o-QMs) from o-hydroxybenzhydryl alcohol. Notably, as a class of readily available and highly active intermediates, o-QMs were first used in the construction of benzofurans. This [4 + 1] cycloaddition reaction provides a straightforward and efficient methodology for the construction of 2-aminobenzofurans scaffold in good yield (up to 93% yield) under mild conditions.
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spelling pubmed-97377622022-12-11 A Novel Method to Construct 2-Aminobenzofurans via [4 + 1] Cycloaddition Reaction of In Situ Generated Ortho-Quinone Methides with Isocyanides Lin, Huaxin Tang, Senling Pan, Yang Liang, Peng Ma, Xiaofeng Jiao, Wei Shao, Huawu Molecules Article A new approach for the synthesis of 2-aminobenzofurans has been described via Sc(OTf)(3) mediated formal cycloaddition of isocyanides with the in situ generated ortho-quinone methides (o-QMs) from o-hydroxybenzhydryl alcohol. Notably, as a class of readily available and highly active intermediates, o-QMs were first used in the construction of benzofurans. This [4 + 1] cycloaddition reaction provides a straightforward and efficient methodology for the construction of 2-aminobenzofurans scaffold in good yield (up to 93% yield) under mild conditions. MDPI 2022-12-04 /pmc/articles/PMC9737762/ /pubmed/36500630 http://dx.doi.org/10.3390/molecules27238538 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Lin, Huaxin
Tang, Senling
Pan, Yang
Liang, Peng
Ma, Xiaofeng
Jiao, Wei
Shao, Huawu
A Novel Method to Construct 2-Aminobenzofurans via [4 + 1] Cycloaddition Reaction of In Situ Generated Ortho-Quinone Methides with Isocyanides
title A Novel Method to Construct 2-Aminobenzofurans via [4 + 1] Cycloaddition Reaction of In Situ Generated Ortho-Quinone Methides with Isocyanides
title_full A Novel Method to Construct 2-Aminobenzofurans via [4 + 1] Cycloaddition Reaction of In Situ Generated Ortho-Quinone Methides with Isocyanides
title_fullStr A Novel Method to Construct 2-Aminobenzofurans via [4 + 1] Cycloaddition Reaction of In Situ Generated Ortho-Quinone Methides with Isocyanides
title_full_unstemmed A Novel Method to Construct 2-Aminobenzofurans via [4 + 1] Cycloaddition Reaction of In Situ Generated Ortho-Quinone Methides with Isocyanides
title_short A Novel Method to Construct 2-Aminobenzofurans via [4 + 1] Cycloaddition Reaction of In Situ Generated Ortho-Quinone Methides with Isocyanides
title_sort novel method to construct 2-aminobenzofurans via [4 + 1] cycloaddition reaction of in situ generated ortho-quinone methides with isocyanides
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9737762/
https://www.ncbi.nlm.nih.gov/pubmed/36500630
http://dx.doi.org/10.3390/molecules27238538
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