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Synthesis of Highly Functionalized 4-Amino-2-(trifluoromethyl)-1H-pyrroles
Synthesis ( IF 2.2 ) Pub Date : 2021-05-10 , DOI: 10.1055/a-1503-9057
Nilo Zanatta , Lucimara L. Zachow , Mateus Mittersteiner , Estefania C. Aquino , Helio G. Bonacorso , Marcos A. P. Martins

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.

中文翻译:

高度官能化的 4-氨基-2-(三氟甲基)-1H-吡咯的合成

在这项工作中,研究了 5-bromo-1,1,1-trifluoro-4-methoxypent-3-en-2-one 对脂肪族伯胺的反应性。发现该反应对合成一系列 1-烷基-4-(氨基烷基)-2-(三氟甲基)-1H-吡咯(13 个实例,产率高达 90%)和一系列高度官能化的 β-烯胺酮(6个例子,产率高达78%),只需要控制胺的量和反应条件。通过单晶 X 射线衍射和 2D NMR 实验明确确定了产物的结构。
更新日期:2021-06-15
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