Access to Indole-Fused Benzannulated Medium-Sized Rings through a Gold(I)-Catalyzed Cascade Cyclization of Azido-Alkynes.
alpha-imino gold(I) carbenes
arylation
gold catalysis
heterocycles
medium-sized rings
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783
Informations de publication
Date de publication:
09 Sep 2021
09 Sep 2021
Historique:
received:
23
05
2021
pubmed:
11
6
2021
medline:
14
9
2021
entrez:
10
6
2021
Statut:
ppublish
Résumé
Because benzannulated and indole-fused medium-sized rings are found in many bioactive compounds, combining these fragments might lead to unexplored areas of biologically relevant and uncovered chemical space. Herein is shown that α-imino gold carbene chemistry can play an important role in solving the difficulty in the formation of medium-sized rings. Namely, phenylene-tethered azido-alkynes undergo arylative cyclization through the formation of a gold carbene intermediate to afford benzannulated indole-fused medium-sized tetracycles. The reactions allow a range of different aryl substitution patterns and efficient access to these otherwise difficult-to-obtain medium-sized rings. This study also demonstrates the feasibility of the semihollow-shaped C-dtbm ligand for the construction of a nine-membered ring.
Identifiants
pubmed: 34110644
doi: 10.1002/chem.202101824
doi:
Substances chimiques
Alkynes
0
Indoles
0
Gold
7440-57-5
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
12992-12997Subventions
Organisme : Japan Society for the Promotion of Science
ID : JP17H03971
Organisme : Japan Society for the Promotion of Science
ID : 20K06938
Organisme : Japan Agency for Medical Research and Development
ID : JP20am0101092j0004
Organisme : Japan Agency for Medical Research and Development
ID : JP20gm1010007
Organisme : Tokyo Biochemical Research Foundation
Informations de copyright
© 2021 Wiley-VCH GmbH.
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It should be noted that the reaction of N-alkyl derivative 1 t resulted in polymerization without producing the desired product 2 t. .