Extended Multicomponent Reactions with Indole Aldehydes: Access to Unprecedented Polyheterocyclic Scaffolds, Ligands of the Aryl Hydrocarbon Receptor.
domino reactions
multicomponent reactions
nitrogen heterocycles
receptors
synthetic methods
Journal
Angewandte Chemie (International ed. in English)
ISSN: 1521-3773
Titre abrégé: Angew Chem Int Ed Engl
Pays: Germany
ID NLM: 0370543
Informations de publication
Date de publication:
01 02 2021
01 02 2021
Historique:
received:
17
08
2020
revised:
30
09
2020
pubmed:
14
10
2020
medline:
2
4
2021
entrez:
13
10
2020
Statut:
ppublish
Résumé
The participation of reactants undergoing a polarity inversion along a multicomponent reaction allows the continuation of the transformation with productive domino processes. Thus, indole aldehydes in Groebke-Blackburn-Bienaymé reactions lead to an initial adduct which spontaneously triggers a series of events leading to the discovery of novel reaction pathways together with direct access to a variety of linked, fused, and bridged polyheterocyclic scaffolds. Indole 3- and 4-carbaldehydes with suitable isocyanides and aminoazines afford fused adducts through oxidative Pictet-Spengler processes, whereas indole 2-carbaldehyde yields linked indolocarbazoles under mild conditions, and a bridged macrocycle at high temperature. These novel structures are potent activators of the human aryl hydrocarbon receptor signaling pathway.
Identifiants
pubmed: 33048416
doi: 10.1002/anie.202011253
doi:
Substances chimiques
Aldehydes
0
Indoles
0
Ligands
0
Receptors, Aryl Hydrocarbon
0
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
2603-2608Informations de copyright
© 2020 Wiley-VCH GmbH.
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CCDC 2019590 (7 a), 2023659 (8 a), 2023664 (11 e), and 2019595 (12) contain the supplementary crystallographic data for this paper. These data are provided free of charge by The Cambridge Crystallographic Data Centre.