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Synthesis of Oxygen Heterocycles via Aromatic C-O Bond Formation Using Arynes
Most of the synthetic approaches to the benzo-fused heterocycles containing an oxygen atom have involved the use of phenol derivatives as a starting material. This review highlights the new synthetic approaches involving the aromatic C-O bond-forming process using arynes. The insertion of arynes int...
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Formato: | Online Artículo Texto |
Lenguaje: | English |
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MDPI
2015
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6332388/ https://www.ncbi.nlm.nih.gov/pubmed/26184140 http://dx.doi.org/10.3390/molecules200712558 |
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author | Miyabe, Hideto |
author_facet | Miyabe, Hideto |
author_sort | Miyabe, Hideto |
collection | PubMed |
description | Most of the synthetic approaches to the benzo-fused heterocycles containing an oxygen atom have involved the use of phenol derivatives as a starting material. This review highlights the new synthetic approaches involving the aromatic C-O bond-forming process using arynes. The insertion of arynes into the C=O bond gives the unstable intermediates, [2 + 2] cycloaddition-type adducts, which can be easily converted into a variety of oxygen atom-containing heterocycles in a single operation. In this review, the syntheses of oxygen heterocycles, such as coumarin, chromene, xanthene, dihydrobenzofuran and benzofuran derivatives, via the insertion of arynes into the C=O bond of aldehydes or formamides are summarized. |
format | Online Article Text |
id | pubmed-6332388 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2015 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-63323882019-01-24 Synthesis of Oxygen Heterocycles via Aromatic C-O Bond Formation Using Arynes Miyabe, Hideto Molecules Review Most of the synthetic approaches to the benzo-fused heterocycles containing an oxygen atom have involved the use of phenol derivatives as a starting material. This review highlights the new synthetic approaches involving the aromatic C-O bond-forming process using arynes. The insertion of arynes into the C=O bond gives the unstable intermediates, [2 + 2] cycloaddition-type adducts, which can be easily converted into a variety of oxygen atom-containing heterocycles in a single operation. In this review, the syntheses of oxygen heterocycles, such as coumarin, chromene, xanthene, dihydrobenzofuran and benzofuran derivatives, via the insertion of arynes into the C=O bond of aldehydes or formamides are summarized. MDPI 2015-07-09 /pmc/articles/PMC6332388/ /pubmed/26184140 http://dx.doi.org/10.3390/molecules200712558 Text en © 2015 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Review Miyabe, Hideto Synthesis of Oxygen Heterocycles via Aromatic C-O Bond Formation Using Arynes |
title | Synthesis of Oxygen Heterocycles via Aromatic C-O Bond Formation Using Arynes |
title_full | Synthesis of Oxygen Heterocycles via Aromatic C-O Bond Formation Using Arynes |
title_fullStr | Synthesis of Oxygen Heterocycles via Aromatic C-O Bond Formation Using Arynes |
title_full_unstemmed | Synthesis of Oxygen Heterocycles via Aromatic C-O Bond Formation Using Arynes |
title_short | Synthesis of Oxygen Heterocycles via Aromatic C-O Bond Formation Using Arynes |
title_sort | synthesis of oxygen heterocycles via aromatic c-o bond formation using arynes |
topic | Review |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6332388/ https://www.ncbi.nlm.nih.gov/pubmed/26184140 http://dx.doi.org/10.3390/molecules200712558 |
work_keys_str_mv | AT miyabehideto synthesisofoxygenheterocyclesviaaromaticcobondformationusingarynes |