Rapid pseudo five-component synthesis of intensively blue luminescent 2,5-di(hetero)arylfurans via a Sonogashira–Glaser cyclization sequence

2,5-Di(hetero)arylfurans are readily accessible in a pseudo five-component reaction via a Sonogashira–Glaser coupling sequence followed by a superbase-mediated (KOH/DMSO) cyclization in a consecutive one-pot fashion. Besides the straightforward synthesis of natural products and biologically active m...

Descripción completa

Detalles Bibliográficos
Autores principales: Klukas, Fabian, Grunwald, Alexander, Menschel, Franziska, Müller, Thomas J J
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2014
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3999768/
https://www.ncbi.nlm.nih.gov/pubmed/24778719
http://dx.doi.org/10.3762/bjoc.10.60
_version_ 1782313535833899008
author Klukas, Fabian
Grunwald, Alexander
Menschel, Franziska
Müller, Thomas J J
author_facet Klukas, Fabian
Grunwald, Alexander
Menschel, Franziska
Müller, Thomas J J
author_sort Klukas, Fabian
collection PubMed
description 2,5-Di(hetero)arylfurans are readily accessible in a pseudo five-component reaction via a Sonogashira–Glaser coupling sequence followed by a superbase-mediated (KOH/DMSO) cyclization in a consecutive one-pot fashion. Besides the straightforward synthesis of natural products and biologically active molecules all representatives are particularly interesting due to their bright blue luminescence with remarkably high quantum yields. The electronic structure of the title compounds is additionally studied with DFT computations.
format Online
Article
Text
id pubmed-3999768
institution National Center for Biotechnology Information
language English
publishDate 2014
publisher Beilstein-Institut
record_format MEDLINE/PubMed
spelling pubmed-39997682014-04-28 Rapid pseudo five-component synthesis of intensively blue luminescent 2,5-di(hetero)arylfurans via a Sonogashira–Glaser cyclization sequence Klukas, Fabian Grunwald, Alexander Menschel, Franziska Müller, Thomas J J Beilstein J Org Chem Full Research Paper 2,5-Di(hetero)arylfurans are readily accessible in a pseudo five-component reaction via a Sonogashira–Glaser coupling sequence followed by a superbase-mediated (KOH/DMSO) cyclization in a consecutive one-pot fashion. Besides the straightforward synthesis of natural products and biologically active molecules all representatives are particularly interesting due to their bright blue luminescence with remarkably high quantum yields. The electronic structure of the title compounds is additionally studied with DFT computations. Beilstein-Institut 2014-03-18 /pmc/articles/PMC3999768/ /pubmed/24778719 http://dx.doi.org/10.3762/bjoc.10.60 Text en Copyright © 2014, Klukas et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Klukas, Fabian
Grunwald, Alexander
Menschel, Franziska
Müller, Thomas J J
Rapid pseudo five-component synthesis of intensively blue luminescent 2,5-di(hetero)arylfurans via a Sonogashira–Glaser cyclization sequence
title Rapid pseudo five-component synthesis of intensively blue luminescent 2,5-di(hetero)arylfurans via a Sonogashira–Glaser cyclization sequence
title_full Rapid pseudo five-component synthesis of intensively blue luminescent 2,5-di(hetero)arylfurans via a Sonogashira–Glaser cyclization sequence
title_fullStr Rapid pseudo five-component synthesis of intensively blue luminescent 2,5-di(hetero)arylfurans via a Sonogashira–Glaser cyclization sequence
title_full_unstemmed Rapid pseudo five-component synthesis of intensively blue luminescent 2,5-di(hetero)arylfurans via a Sonogashira–Glaser cyclization sequence
title_short Rapid pseudo five-component synthesis of intensively blue luminescent 2,5-di(hetero)arylfurans via a Sonogashira–Glaser cyclization sequence
title_sort rapid pseudo five-component synthesis of intensively blue luminescent 2,5-di(hetero)arylfurans via a sonogashira–glaser cyclization sequence
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3999768/
https://www.ncbi.nlm.nih.gov/pubmed/24778719
http://dx.doi.org/10.3762/bjoc.10.60
work_keys_str_mv AT klukasfabian rapidpseudofivecomponentsynthesisofintensivelyblueluminescent25diheteroarylfuransviaasonogashiraglasercyclizationsequence
AT grunwaldalexander rapidpseudofivecomponentsynthesisofintensivelyblueluminescent25diheteroarylfuransviaasonogashiraglasercyclizationsequence
AT menschelfranziska rapidpseudofivecomponentsynthesisofintensivelyblueluminescent25diheteroarylfuransviaasonogashiraglasercyclizationsequence
AT mullerthomasjj rapidpseudofivecomponentsynthesisofintensivelyblueluminescent25diheteroarylfuransviaasonogashiraglasercyclizationsequence

Ejemplares similares