Marina V. Goryaeva, Anna E. Ivanova, Yanina V. Burgart, Olesya A. Bakhareva, Marina A. Ezhikova, Mikhail I. Kodess, Pavel A. Slepukhin, Ksenia O. Malysheva, Olga P. Krasnykh, Aleksandrina S. Volobueva, Margarita A. Zinovieva, Mikhail G. Mikhalski, Victor I. Saloutin
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引用次数: 0
Abstract
To synthesize persubstituted, alkylene‐bridged, and heterofused CF3‐γ‐lactams, a domino strategy based on the multicomponent reaction of ethyl trifluoropyruvate and diethyl ketone with N,N‐ and N,O‐dinucleophilic reagents was developed. The structure of the final products depends on both the reaction conditions and the reagent ratio. It was found that bicyclic γ‐lactams and pyrrolidin‐2‐ones are predominantly formed under catalyst‐free conditions, whereas dual acid–base catalysis promotes the formation of N‐hydroxyalkyl‐substituted dihydropyrrol‐2‐ones and bis(dihydropyrrol‐2‐one) derivatives linked by an alkylene bridge. The diastereomeric structures of the newly synthesized CF3‐γ‐lactams were established by 1H, 19F, and 13C NMR spectroscopy, including two‐dimensional NMR experiments, as well as by x‐ray crystallographic analysis. A plausible mechanism for the multicomponent reaction is proposed and supported by additional synthetic experiments. Among the synthesized compounds, several derivatives exhibited analgesic and antiviral activities.
To synthesize persubstituted, alkylene‐bridged, and heterofused CF3‐γ‐lactams, a domino strategy based on the multicomponent reaction of ethyl trifluoropyruvate and diethyl ketone with N,N‐ and N,O‐dinucleophilic reagents was developed. The structure of the final products depends on both the reaction conditions and the reagent ratio. It was found that bicyclic γ‐lactams and pyrrolidin‐2‐ones are predominantly formed under catalyst‐free conditions, whereas dual acid–base catalysis promotes the formation of N‐hydroxyalkyl‐substituted dihydropyrrol‐2‐ones and bis(dihydropyrrol‐2‐one) derivatives linked by an alkylene bridge. The diastereomeric structures of the newly synthesized CF3‐γ‐lactams were established by 1H, 19F, and 13C NMR spectroscopy, including two‐dimensional NMR experiments, as well as by x‐ray crystallographic analysis. A plausible mechanism for the multicomponent reaction is proposed and supported by additional synthetic experiments. Among the synthesized compounds, several derivatives exhibited analgesic and antiviral activities.
The multicomponent domino reaction of ethyl trifluoropyruvate and diethyl ketone with diamines/amino alcohols is an effective method for the synthesis of various CF3‐γ‐lactams. Their structure varies depending on the dinucleophile and conditions. The pharmacological potential of new γ‐lactams is shown.
以三氟丙酮酸乙酯和二乙基酮与N，N-和N， o -二核试剂为多组分反应为基础，采用多米诺骨牌策略合成过取代、烷基桥接和杂聚的CF3-γ-内酰胺。最终产物的结构取决于反应条件和试剂配比。双环γ-内酰胺和吡咯烷酮主要在无催化剂条件下生成，而双酸碱催化则促进n-羟基烷基取代的二氢吡咯烷酮和由烷基桥连接的双（二氢吡咯烷酮）衍生物的生成。通过1H、19F和13C核磁共振波谱，包括二维核磁共振实验，以及x射线晶体学分析，确定了新合成的CF3-γ-内酰胺的非对映体结构。提出了一种合理的多组分反应机理，并得到了其他合成实验的支持。在合成的化合物中，几种衍生物具有镇痛和抗病毒活性。
期刊介绍：
Organic chemistry is the fundamental science that stands at the heart of chemistry, biology, and materials science. Research in these areas is vigorous and truly international, with three major regions making almost equal contributions: America, Europe and Asia. Asia now has its own top international organic chemistry journal—the Asian Journal of Organic Chemistry (AsianJOC)
The AsianJOC is designed to be a top-ranked international research journal and publishes primary research as well as critical secondary information from authors across the world. The journal covers organic chemistry in its entirety. Authors and readers come from academia, the chemical industry, and government laboratories.
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