Synthesis of Elaborate Benzofuran-2-carboxamide Derivatives through a Combination of 8-Aminoquinoline Directed C-H Arylation and Transamidation Chemistry.
8-aminoquinoline
C–H functionalization
benzofuran
palladium
transamidation
Journal
Molecules (Basel, Switzerland)
ISSN: 1420-3049
Titre abrégé: Molecules
Pays: Switzerland
ID NLM: 100964009
Informations de publication
Date de publication:
15 Jan 2020
15 Jan 2020
Historique:
received:
20
12
2019
revised:
09
01
2020
accepted:
13
01
2020
entrez:
19
1
2020
pubmed:
19
1
2020
medline:
27
10
2020
Statut:
epublish
Résumé
Herein, we present a short and highly modular synthetic route that involves 8-aminoquinoline directed C-H arylation and transamidation chemistry, and which enables access to a wide range of elaborate benzofuran-2-carboxamides. For the directed C-H arylation reactions, Pd catalysis was used to install a wide range of aryl and heteroaryl substituents at the C3 position of the benzofuran scaffold in high efficiency. Directing group cleavage and further diversification of the C3-arylated benzofuran products were then achieved in a single synthetic operation through the utilization of a one-pot, two-step transamidation procedure, which proceeded via the intermediate
Identifiants
pubmed: 31952313
pii: molecules25020361
doi: 10.3390/molecules25020361
pmc: PMC7024369
pii:
doi:
Substances chimiques
Amides
0
Aminoquinolines
0
Benzene Derivatives
0
Benzofurans
0
benzofuran
LK6946W774
8-aminoquinoline
U34EAV21TG
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Subventions
Organisme : Wenner-Gren Foundation
ID : FT2018-0002
Organisme : Stiftelsen Olle Engkvist Byggmästare
ID : 191435
Organisme : Magnus Bergvalls Stiftelse
ID : 2018-02583
Déclaration de conflit d'intérêts
The authors declare no conflict of interest.
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