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- Title
Substituent-Controllable Cascade Regioselective Annulation of β -Enaminones with N -Sulfonyl Triazoles for Modular Access to Imidazoles and Pyrroles.
- Authors
Wang, Hua; Zhou, Tongtong; Wu, Mengdi; Ye, Qingqing; He, Xinwei
- 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 β-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.
- Subjects
PYRROLES; TRIAZOLES; ANNULATION; IMIDAZOLES; AMINO group; METHYL groups; PYRROLE derivatives
- Publication
Molecules, 2023, Vol 28, Issue 11, p4416
- ISSN
1420-3049
- Publication type
Article
- DOI
10.3390/molecules28114416