Multicomponent Petasis Reaction for the Synthesis of Functionalized 2-Aminothiophenes and Thienodiazepines.
2-aminothiophenes
Petasis reaction
multicomponent reaction
small molecules
thienodiazepines
Journal
ACS combinatorial science
ISSN: 2156-8944
Titre abrégé: ACS Comb Sci
Pays: United States
ID NLM: 101540531
Informations de publication
Date de publication:
12 10 2020
12 10 2020
Historique:
pubmed:
29
9
2020
medline:
10
9
2021
entrez:
28
9
2020
Statut:
ppublish
Résumé
Multicomponent Petasis reaction has been widely applied for the synthesis of functionalized amine building blocks and biologically active compounds. Employing primary aromatic amines that are not typical reactive substrates contributes to expand the application scope of the Petasis reaction. In this study, we demonstrated the synthesis of functionalized 2-aminothiophenes using Gewald-reaction-derived 2-aminothiophenes as the amine substrates, whose low reactivity in the Petasis reaction was overcome using hexafluoro-2-propanol as the solvent in a mild condition. The obtained Petasis products are amenable for further transformations owing to the presence of multiple functional handles. A following intramolecular cyclization of selected Petasis products afforded substituted tricyclic heterocycles that incorporate a pharmaceutically interesting thienodiazepine moiety.
Identifiants
pubmed: 32985878
doi: 10.1021/acscombsci.0c00173
pmc: PMC7584359
doi:
Substances chimiques
Amines
0
Azepines
0
Propanols
0
Small Molecule Libraries
0
Solvents
0
Thiophenes
0
thienodiazepine substance
0
hexafluoroisopropanol
3D632GYQ50
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
495-499Références
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