N‐Functionalization of 4‐amino‐2‐(trifluoromethyl)‐1H‐pyrroles: Synthesis of N‐alkyl derivatives and 1,2,3‐triazol‐4‐yl‐pyrrole scaffolds

The N‐functionalization of 4‐amino‐2‐trifluoromethyl‐1H‐pyrroles using alkyl halides is reported. The selectivity of the alkylation reaction was highly dependent on the nature of the alkyl halide and the reaction conditions applied, that is, methyl iodide may furnish N‐methyl or N,N‐dimethyl pyrrole...

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Bibliographic Details
Published in:Journal of heterocyclic chemistry 2022-08, Vol.59 (8), p.1308-1319
Main Authors: Zachow, Lucimara L., Mittersteiner, Mateus, Bonacorso, Helio G., Martins, Marcos A. P., Zanatta, Nilo
Format: Article
Language:English
Subjects:
Alkylation
Halides
NMR
Nuclear magnetic resonance
Pyrroles
Selectivity
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Summary:The N‐functionalization of 4‐amino‐2‐trifluoromethyl‐1H‐pyrroles using alkyl halides is reported. The selectivity of the alkylation reaction was highly dependent on the nature of the alkyl halide and the reaction conditions applied, that is, methyl iodide may furnish N‐methyl or N,N‐dimethyl pyrroles, while allyl bromide furnishes N‐allyl or N,C‐diallyl analogs and propargyl bromide furnishes exclusively N‐propargyl pyrroles. The alkylated products were obtained between 65%–90% yields and were subjected to CuAAC reactions, which furnished conjugated 1,2,3‐triazoles in good yields (72%–91%). The structures of the obtained compounds were unambiguously determined via 2D‐NMR experiments. The N‐/C‐ alkylation of 4‐amino‐2‐(trifluoromethyl)‐1H‐pyrroles with alkyl halides was carried out in good yields. The selectivity of the reaction was also investigated and, lastly, triazole–pyrrole scaffolds were prepared.
ISSN:0022-152X
1943-5193
DOI:10.1002/jhet.4468