N‐Functionalization of 4‐amino‐2‐(trifluoromethyl)‐1H‐pyrroles: Synthesis of N‐alkyl derivatives and 1, 2, 3‐triazol‐4‐yl‐pyrrole scaffolds. (1st March 2022)

• Record Type: Journal Article
• Authors: Zachow, Lucimara L.; Mittersteiner, Mateus; Bonacorso, Helio G.; Martins, Marcos A. P.; Zanatta, Nilo
• Is Part Of: Journal of heterocyclic chemistry. Volume 59:Number 8(2022)
• Page Start: 1308
• Page End: 1319
• Publication Date: 2022-03-01
• Subjects: Heterocyclic compounds -- Periodicals; 547.59
• DOI: 10.1002/jhet.4468
• Languages: English
• ISSNs: 0022-152X

Abstract

Abstract: The N ‐functionalization of 4‐amino‐2‐trifluoromethyl‐1 H ‐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. Abstract : The N ‐/ C ‐ alkylation of 4‐amino‐2‐(trifluoromethyl)‐1 H ‐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.