β-氟代-β-硝基苯乙烯合成单氟代吡咯衍生物的简便方法。
An Easy Synthesis of Monofluorinated Derivatives of Pyrroles from β-Fluoro-β-Nitrostyrenes.
机构信息
Department of Chemistry, Lomonosov Moscow State University, Leninskie Gory 1, 119991 Moscow, Russia.
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prosp. 47, 119991 Moscow, Russia.
出版信息
Molecules. 2021 Jun 9;26(12):3515. doi: 10.3390/molecules26123515.
The catalyst-free conjugate addition of pyrroles to β-Fluoro-β-nitrostyrenes was investigated. The reaction was found to proceed under solvent-free conditions to form 2-(2-Fluoro-2-nitro-1-arylethyl)-1-pyrroles. The effectiveness of this approach was demonstrated through the preparation of a series of the target products in a quantitative yield. The kinetics of a conjugate addition of pyrrole was studied in detail to reveal the substituent effect and activation parameters of the reaction. The subsequent base-induced elimination of nitrous acid afforded a series of novel 2-(2-Fluoro-1-arylvinyl)-1-pyrroles prepared in up to an 85% isolated yield. The two-step sequence herein proposed is an indispensable alternative to a direct reaction with elusive and unstable 1-Fluoroacetylenes.
研究了吡咯与β-氟代-β-硝基苯乙烯的无催化剂共轭加成反应。反应在无溶剂条件下进行，生成 2-(2-氟-2-硝基-1-芳基乙基)-1-吡咯。通过定量收率制备一系列目标产物证明了该方法的有效性。详细研究了吡咯的共轭加成动力学，以揭示反应的取代基效应和活化参数。随后，亚硝酸的碱诱导消除生成了一系列新型 2-(2-氟-1-芳基乙烯基)-1-吡咯，收率高达 85%。本文提出的两步序列是与难以获得且不稳定的 1-氟乙炔直接反应的不可或缺的替代方法。
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