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1,3- and 1,4-Benzdiyne equivalents for regioselective synthesis of polycyclic heterocycles
We have devised a novel 1,3-benzdiyne equivalent, capable of quadruple functionalization by sequential benzyne generation and reaction with arynophiles. The key features of this method include the chemoselective generation of two triple bonds in a single benzene ring under fluoride-mediated mild con...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
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Royal Society of Chemistry
2016
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6020534/ https://www.ncbi.nlm.nih.gov/pubmed/30155171 http://dx.doi.org/10.1039/c6sc00798h |
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author | Ikawa, Takashi Masuda, Shigeaki Takagi, Akira Akai, Shuji |
author_facet | Ikawa, Takashi Masuda, Shigeaki Takagi, Akira Akai, Shuji |
author_sort | Ikawa, Takashi |
collection | PubMed |
description | We have devised a novel 1,3-benzdiyne equivalent, capable of quadruple functionalization by sequential benzyne generation and reaction with arynophiles. The key features of this method include the chemoselective generation of two triple bonds in a single benzene ring under fluoride-mediated mild conditions, and the regiocontrol of each benzyne reaction by the substituent next to the triple bond. This method produced various benzo-fused heteroaromatic compounds via reactions with arynophiles, such as furans, azides, and diazo compounds. A validation of the method is given in the convergent synthesis of the antipsychotic drug risperidone. A similar strategy has also been applied to a 1,4-benzdiyne equivalent to construct linearly benzo-fused heteroaromatics. |
format | Online Article Text |
id | pubmed-6020534 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2016 |
publisher | Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
spelling | pubmed-60205342018-08-28 1,3- and 1,4-Benzdiyne equivalents for regioselective synthesis of polycyclic heterocycles Ikawa, Takashi Masuda, Shigeaki Takagi, Akira Akai, Shuji Chem Sci Chemistry We have devised a novel 1,3-benzdiyne equivalent, capable of quadruple functionalization by sequential benzyne generation and reaction with arynophiles. The key features of this method include the chemoselective generation of two triple bonds in a single benzene ring under fluoride-mediated mild conditions, and the regiocontrol of each benzyne reaction by the substituent next to the triple bond. This method produced various benzo-fused heteroaromatic compounds via reactions with arynophiles, such as furans, azides, and diazo compounds. A validation of the method is given in the convergent synthesis of the antipsychotic drug risperidone. A similar strategy has also been applied to a 1,4-benzdiyne equivalent to construct linearly benzo-fused heteroaromatics. Royal Society of Chemistry 2016-08-01 2016-04-18 /pmc/articles/PMC6020534/ /pubmed/30155171 http://dx.doi.org/10.1039/c6sc00798h Text en This journal is © The Royal Society of Chemistry 2016 http://creativecommons.org/licenses/by/3.0/ This article is freely available. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence (CC BY 3.0) |
spellingShingle | Chemistry Ikawa, Takashi Masuda, Shigeaki Takagi, Akira Akai, Shuji 1,3- and 1,4-Benzdiyne equivalents for regioselective synthesis of polycyclic heterocycles |
title | 1,3- and 1,4-Benzdiyne equivalents for regioselective synthesis of polycyclic heterocycles
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title_full | 1,3- and 1,4-Benzdiyne equivalents for regioselective synthesis of polycyclic heterocycles
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title_fullStr | 1,3- and 1,4-Benzdiyne equivalents for regioselective synthesis of polycyclic heterocycles
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title_full_unstemmed | 1,3- and 1,4-Benzdiyne equivalents for regioselective synthesis of polycyclic heterocycles
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title_short | 1,3- and 1,4-Benzdiyne equivalents for regioselective synthesis of polycyclic heterocycles
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title_sort | 1,3- and 1,4-benzdiyne equivalents for regioselective synthesis of polycyclic heterocycles |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6020534/ https://www.ncbi.nlm.nih.gov/pubmed/30155171 http://dx.doi.org/10.1039/c6sc00798h |
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