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Synthesis 2021; 53(16): 2841-2849
DOI: 10.1055/a-1503-9057
DOI: 10.1055/a-1503-9057
paper
Synthesis of Highly Functionalized 4-Amino-2-(trifluoromethyl)-1H-pyrroles
The authors are grateful for financial support from the Fundação de Amparo à Pesquisa do Estado do Rio Grande do Sul (FAPERGS/CNPq – PRONEX, grant no. 16/2551-0000477-3) and Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq, grant no. 407898/2018-2), and for fellowships from Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES) (L.L.Z., M.M., E.C.A.) and CNPq (H.G.B., M.A.P.M., N.Z.).
Abstract
In this work, the reactivity of 5-bromo-1,1,1-trifluoro-4-methoxypent-3-en-2-one toward primary aliphatic amines was studied. The reaction was found to be extremely selective to synthesize a series of 1-alkyl-4-(aminoalkyl)-2-(trifluoromethyl)-1H-pyrroles (13 examples, up to 90% yield) and a series of highly functionalized β-enaminones (6 examples, up to 78% yield), with only the amount of amine and the reaction conditions needing to be controlled. The structure of the products was unambiguously determined by single crystal X-ray diffraction and 2D NMR experiments.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1503-9057.
- Supporting Information
Publication History
Received: 19 April 2021
Accepted after revision: 10 May 2021
Accepted Manuscript online:
10 May 2021
Article published online:
14 June 2021
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