Substituent-Controllable Cascade Regioselective Annulation of ß-Enaminones with N-Sulfonyl Triazoles for Modular Access to Imidazoles and Pyrroles.
Molecules
; 28(11)2023 May 29.
Article
en En
| MEDLINE
| ID: mdl-37298892
ABSTRACT
A controllable synthesis of trisubstituted imidazoles and pyrroles has been developed through rhodium(II)-catalyzed regioselective annulation of N-sulfonyl-1,2,3-trizaoles with ß-enaminones. The imidazole ring was formed through a 1,1-insertion of the N-H bond to α-imino rhodium carbene, followed by a subsequent intramolecular 1,4-conjugate addition. This occurred when the α-carbon atom of the amino group was bearing a methyl group. Additionally, the pyrrole ring was constructed by utilizing a phenyl substituent and undergoing intramolecular nucleophilic addition. The mild conditions, good tolerance towards functional groups, gram-scale synthesis capability, and ability to undergo valuable transformations of the products qualify this unique protocol as an efficient tool for the synthesis of N-heterocycles.
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Texto completo:
1
Bases de datos:
MEDLINE
Asunto principal:
Pirroles
/
Rodio
Idioma:
En
Revista:
Molecules
Asunto de la revista:
BIOLOGIA
Año:
2023
Tipo del documento:
Article
País de afiliación:
China