Application of the Meerwein reaction of 1,4-benzoquinone to a metal-free synthesis of benzofuropyridine analogues

Several new heterocyclic systems based on a hydroxybenzofuro[2,3-b]pyridine building block were prepared. This benzofuropyridine is easily available from the Meerwein reaction of benzoquinone and a heterocyclic diazonium salt, followed by reduction and cyclization. Electrophilic substitution and fur...

Descripción completa

Detalles Bibliográficos
Autores principales: Singh, Rashmi, Horsten, Tomas, Prakash, Rashmi, Dey, Swapan, Dehaen, Wim
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2021
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8093549/
https://www.ncbi.nlm.nih.gov/pubmed/33981368
http://dx.doi.org/10.3762/bjoc.17.79
_version_ 1783687832725880832
author Singh, Rashmi
Horsten, Tomas
Prakash, Rashmi
Dey, Swapan
Dehaen, Wim
author_facet Singh, Rashmi
Horsten, Tomas
Prakash, Rashmi
Dey, Swapan
Dehaen, Wim
author_sort Singh, Rashmi
collection PubMed
description Several new heterocyclic systems based on a hydroxybenzofuro[2,3-b]pyridine building block were prepared. This benzofuropyridine is easily available from the Meerwein reaction of benzoquinone and a heterocyclic diazonium salt, followed by reduction and cyclization. Electrophilic substitution and further condensations give polycyclic systems, including oxazolo- and chromeno-fused analogues.
format Online
Article
Text
id pubmed-8093549
institution National Center for Biotechnology Information
language English
publishDate 2021
publisher Beilstein-Institut
record_format MEDLINE/PubMed
spelling pubmed-80935492021-05-11 Application of the Meerwein reaction of 1,4-benzoquinone to a metal-free synthesis of benzofuropyridine analogues Singh, Rashmi Horsten, Tomas Prakash, Rashmi Dey, Swapan Dehaen, Wim Beilstein J Org Chem Full Research Paper Several new heterocyclic systems based on a hydroxybenzofuro[2,3-b]pyridine building block were prepared. This benzofuropyridine is easily available from the Meerwein reaction of benzoquinone and a heterocyclic diazonium salt, followed by reduction and cyclization. Electrophilic substitution and further condensations give polycyclic systems, including oxazolo- and chromeno-fused analogues. Beilstein-Institut 2021-04-30 /pmc/articles/PMC8093549/ /pubmed/33981368 http://dx.doi.org/10.3762/bjoc.17.79 Text en Copyright © 2021, Singh et al. https://creativecommons.org/licenses/by/4.0/https://www.beilstein-journals.org/bjoc/terms/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0 (https://creativecommons.org/licenses/by/4.0/) ). Please note that the reuse, redistribution and reproduction in particular requires that the author(s) and source are credited and that individual graphics may be subject to special legal provisions. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms/terms)
spellingShingle Full Research Paper
Singh, Rashmi
Horsten, Tomas
Prakash, Rashmi
Dey, Swapan
Dehaen, Wim
Application of the Meerwein reaction of 1,4-benzoquinone to a metal-free synthesis of benzofuropyridine analogues
title Application of the Meerwein reaction of 1,4-benzoquinone to a metal-free synthesis of benzofuropyridine analogues
title_full Application of the Meerwein reaction of 1,4-benzoquinone to a metal-free synthesis of benzofuropyridine analogues
title_fullStr Application of the Meerwein reaction of 1,4-benzoquinone to a metal-free synthesis of benzofuropyridine analogues
title_full_unstemmed Application of the Meerwein reaction of 1,4-benzoquinone to a metal-free synthesis of benzofuropyridine analogues
title_short Application of the Meerwein reaction of 1,4-benzoquinone to a metal-free synthesis of benzofuropyridine analogues
title_sort application of the meerwein reaction of 1,4-benzoquinone to a metal-free synthesis of benzofuropyridine analogues
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8093549/
https://www.ncbi.nlm.nih.gov/pubmed/33981368
http://dx.doi.org/10.3762/bjoc.17.79
work_keys_str_mv AT singhrashmi applicationofthemeerweinreactionof14benzoquinonetoametalfreesynthesisofbenzofuropyridineanalogues
AT horstentomas applicationofthemeerweinreactionof14benzoquinonetoametalfreesynthesisofbenzofuropyridineanalogues
AT prakashrashmi applicationofthemeerweinreactionof14benzoquinonetoametalfreesynthesisofbenzofuropyridineanalogues
AT deyswapan applicationofthemeerweinreactionof14benzoquinonetoametalfreesynthesisofbenzofuropyridineanalogues
AT dehaenwim applicationofthemeerweinreactionof14benzoquinonetoametalfreesynthesisofbenzofuropyridineanalogues

Ejemplares similares