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Pictet–Spengler Synthesis of Perfluoroalkylated Tetrahydro-γ-carbolines and Tetrahydropyrrolopyrazines
Synthesis ( IF 2.2 ) Pub Date : 2019-10-28 , DOI: 10.1055/s-0039-1690729
Natalia G. Voznesenskaia , Olga I. Shmatova , Valentine G. Nenajdenko 1
Synthesis ( IF 2.2 ) Pub Date : 2019-10-28 , DOI: 10.1055/s-0039-1690729
Natalia G. Voznesenskaia , Olga I. Shmatova , Valentine G. Nenajdenko 1
Affiliation
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A new method for the synthesis of perfluoroalkylated derivatives of γ-carboline and pyrrolopyrazine was elaborated. Pictet–Spengler reaction of isotryptamine and 2-(pyrrol-1-yl)ethanamine with trifluoromethylated carbonyls and 2-perfluoroalkyl-substituted five-, six-, and seven-membered cyclic imines was studied. It was found that this approach opens efficient access to a family of alkaloid-like compounds bearing a CF3 or C2F5 group in the structure. In the case of the iso-Pictet–Spengler reaction with 2-perfluoroalkyl-substituted cyclic imines, a series of γ-carbolines bearing an aminoalkyl group were prepared.
中文翻译:
Pictet-Spengler合成全氟烷基化的四氢-γ-咔啉和四氢吡咯并吡嗪
阐述了合成γ-咔啉和吡咯并吡嗪全氟烷基化衍生物的新方法。研究了异色胺和2-(吡咯-1-基)乙胺与三氟甲基化羰基和2-全氟烷基取代的五元,六元和七元亚胺的Pictet-Spengler反应。已经发现,该方法打开了对结构中带有CF 3或C 2 F 5基团的生物碱样化合物家族的有效访问的途径。在与2-全氟烷基取代的环亚胺进行iso-Pictet-Spengler反应的情况下,制备了一系列带有氨基烷基的γ-咔啉。
更新日期:2019-10-29
中文翻译:

Pictet-Spengler合成全氟烷基化的四氢-γ-咔啉和四氢吡咯并吡嗪
阐述了合成γ-咔啉和吡咯并吡嗪全氟烷基化衍生物的新方法。研究了异色胺和2-(吡咯-1-基)乙胺与三氟甲基化羰基和2-全氟烷基取代的五元,六元和七元亚胺的Pictet-Spengler反应。已经发现,该方法打开了对结构中带有CF 3或C 2 F 5基团的生物碱样化合物家族的有效访问的途径。在与2-全氟烷基取代的环亚胺进行iso-Pictet-Spengler反应的情况下,制备了一系列带有氨基烷基的γ-咔啉。