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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...

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Autores principales: Ikawa, Takashi, Masuda, Shigeaki, Takagi, Akira, Akai, Shuji
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2016
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.
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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
title_full 1,3- and 1,4-Benzdiyne equivalents for regioselective synthesis of polycyclic heterocycles
title_fullStr 1,3- and 1,4-Benzdiyne equivalents for regioselective synthesis of polycyclic heterocycles
title_full_unstemmed 1,3- and 1,4-Benzdiyne equivalents for regioselective synthesis of polycyclic heterocycles
title_short 1,3- and 1,4-Benzdiyne equivalents for regioselective synthesis of polycyclic heterocycles
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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