Intramolecular azavinyl carbene-triggered rearrangement of furans

An intramolecular rhodium-catalyzed reaction of 1-tosyl-1,2,3-triazoles with furans has been explored. The tosylimino functionality was found to play a significant chemical role participating in the subsequent domino-transformations of a key reaction intermediate. One of the reaction pathways leads...

Descripción completa

Detalles Bibliográficos
Autores principales: Makarov, Anton S., Uchuskin, Maxim G., Hashmi, A. Stephen K.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2019
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6839507/
https://www.ncbi.nlm.nih.gov/pubmed/31803433
http://dx.doi.org/10.1039/c9sc02299f
_version_ 1783467437577994240
author Makarov, Anton S.
Uchuskin, Maxim G.
Hashmi, A. Stephen K.
author_facet Makarov, Anton S.
Uchuskin, Maxim G.
Hashmi, A. Stephen K.
author_sort Makarov, Anton S.
collection PubMed
description An intramolecular rhodium-catalyzed reaction of 1-tosyl-1,2,3-triazoles with furans has been explored. The tosylimino functionality was found to play a significant chemical role participating in the subsequent domino-transformations of a key reaction intermediate. One of the reaction pathways leads to valuable 2-formyl- and 2-acetylpyridine building blocks, which could be obtained in one-pot starting from easily accessible (furan-2-ylmethyl)propargyl amines. An original method for the synthesis of highly functionalized indolizines from the obtained pyridines has been proposed.
format Online
Article
Text
id pubmed-6839507
institution National Center for Biotechnology Information
language English
publishDate 2019
publisher Royal Society of Chemistry
record_format MEDLINE/PubMed
spelling pubmed-68395072019-12-04 Intramolecular azavinyl carbene-triggered rearrangement of furans Makarov, Anton S. Uchuskin, Maxim G. Hashmi, A. Stephen K. Chem Sci Chemistry An intramolecular rhodium-catalyzed reaction of 1-tosyl-1,2,3-triazoles with furans has been explored. The tosylimino functionality was found to play a significant chemical role participating in the subsequent domino-transformations of a key reaction intermediate. One of the reaction pathways leads to valuable 2-formyl- and 2-acetylpyridine building blocks, which could be obtained in one-pot starting from easily accessible (furan-2-ylmethyl)propargyl amines. An original method for the synthesis of highly functionalized indolizines from the obtained pyridines has been proposed. Royal Society of Chemistry 2019-07-26 /pmc/articles/PMC6839507/ /pubmed/31803433 http://dx.doi.org/10.1039/c9sc02299f Text en This journal is © The Royal Society of Chemistry 2019 http://creativecommons.org/licenses/by-nc/3.0/ This article is freely available. This article is licensed under a Creative Commons Attribution Non Commercial 3.0 Unported Licence (CC BY-NC 3.0)
spellingShingle Chemistry
Makarov, Anton S.
Uchuskin, Maxim G.
Hashmi, A. Stephen K.
Intramolecular azavinyl carbene-triggered rearrangement of furans
title Intramolecular azavinyl carbene-triggered rearrangement of furans
title_full Intramolecular azavinyl carbene-triggered rearrangement of furans
title_fullStr Intramolecular azavinyl carbene-triggered rearrangement of furans
title_full_unstemmed Intramolecular azavinyl carbene-triggered rearrangement of furans
title_short Intramolecular azavinyl carbene-triggered rearrangement of furans
title_sort intramolecular azavinyl carbene-triggered rearrangement of furans
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6839507/
https://www.ncbi.nlm.nih.gov/pubmed/31803433
http://dx.doi.org/10.1039/c9sc02299f
work_keys_str_mv AT makarovantons intramolecularazavinylcarbenetriggeredrearrangementoffurans
AT uchuskinmaximg intramolecularazavinylcarbenetriggeredrearrangementoffurans
AT hashmiastephenk intramolecularazavinylcarbenetriggeredrearrangementoffurans

Ejemplares similares