From Umpolung to Alternation: Modified Reactivity of Donor-Acceptor Cyclopropanes Towards Nucleophiles in Reaction with Nitroalkanes

Budynina Ekaterina M.; Ivanov Konstantin L.; Chagarovskiy Alexey O.; Rybakov Victor B.; Trushkov Igor V.; Melnikov Mikhail Ya.

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From Umpolung to Alternation: Modified Reactivity of Donor-Acceptor Cyclopropanes Towards Nucleophiles in Reaction with Nitroalkanes

机译：从Umpolung到交替：与硝基烷反应的供体-受体环丙烷对亲核试剂的修饰反应性

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A conceptually new type of donor-acceptor cyclopropane reactivity towards nucleophiles has been disclosed. An essential characteristic of the process is an unusual nucleophilic attack on the C(3)-position of a cyclopropane, combined with typical small ring-opening by cleavage of the C(1)-C(2) bond between the acceptor and the donor. Based on this new reaction between cyclopropane-1,1-diesters and nitroalkanes, we developed a convenient approach to -nitroesters that can be efficiently transformed to the substituted pyrrolidones, structural analogues of racetame family drugs (rolipram, phenylpiracetam, etc.).

机译：已经公开了概念上新型的供体-受体环丙烷对亲核试剂的反应性。该过程的一个基本特征是对环丙烷的C（3）位置的不寻常亲核攻击，以及通过裂解受体和供体之间的C（1）-C（2）键而形成的典型的小开环。基于环丙烷-1,1-二酯和硝基烷之间的新反应，我们开发了一种简便的方法-硝基酯，可以有效地转化为取代的吡咯烷酮，消旋体家族药物的结构类似物（咯利普兰，苯基吡乙酰胺等）。

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《Chemistry: A European journal》 |2016年第11期|共5页
作者
Budynina Ekaterina M.; Ivanov Konstantin L.; Chagarovskiy Alexey O.; Rybakov Victor B.; Trushkov Igor V.; Melnikov Mikhail Ya.;
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正文语种 eng
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heterocyclic compounds; nitro compounds; nucleophilic addition; pyrrolidones; small rings;

机译：杂环化合物;硝基化合物;亲核加成;吡咯烷酮;小环;

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1. From Umpolung to Alternation: Modified Reactivity of Donor-Acceptor Cyclopropanes Towards Nucleophiles in Reaction with Nitroalkanes [J] . Budynina Ekaterina M., Ivanov Konstantin L., Chagarovskiy Alexey O., Chemistry: A European journal . 2016,第11期

机译：从Umpolung到交替：与硝基烷反应的供体-受体环丙烷对亲核试剂的修饰反应性
2. From Umpolung to Alternation: Modified Reactivity of Donor-Acceptor Cyclopropanes Towards Nucleophiles in Reaction with Nitroalkanes [J] . Budynina Ekaterina M., Ivanov Konstantin L., Chagarovskiy Alexey O., Chemistry: A European journal . 2016,第11期

机译：从Umpolung到交替：与硝基烷反应的供体-受体环丙烷对亲核试剂的修饰反应性
3. Palladium-Catalyzed Reactions of Allylic Boronic Esters with Nucleophiles: Novel Umpolung Reactivity [J] . Unsworth Phillip J., Loeffler Lorenz E., Noble Adam, Synlett . 2015,第11期

机译：烯丙基硼酯与亲核试剂的钯催化反应：新型Umpolung反应性
4. Synthesis of Oxindoles Using Umpolung Amination/Cyclization Reactions of 1H-Indazole-3-carboxylates [C] . Mayuko Mori, Isao Mizota, Makoto Shimizu 日本化学会春季年会講演予稿集 . 2018

机译：使用Umpolung胺化/环化反应的氧吲哚/环化反应的合成1H-吲唑-3-羧酸盐
5. Umpolung Amide Synthesis Mechanistic Studies, Development of a New N-Aryl Amide Synthesis, and α-Oxy- and α-Thio-Nitroalkanes in the Bam-Catalyzed Aza-Henry Reaction [D] . Crocker, Michael. 2021

机译：umpolung酰胺合成机械研究，在Bam催化的Aza-henry反应中开发新的N-芳基合成，α-氧 - 和α-硫代 - 硝基烷烃
6. Electrophilically Activated Nitroalkanes in Reactions With Carbon Based Nucleophiles [O] . Nicolai A. Aksenov, Alexander V. Aksenov, Sergei N. Ovcharov, 2020

机译：与碳基亲核试剂反应的亲电子活化的硝基烷
7. Electrophilically Activated Nitroalkanes in Reactions With Carbon Based Nucleophiles [O] . Nicolai A. Aksenov, Alexander V. Aksenov, Sergei N. Ovcharov, 2020

机译：在与碳基亲核试剂的反应中电泳活化的硝基烷烃
8. Laser Kinetic Spectroscopic Studies of (a) The Unimolecular Reactions of Nitroalkanes and, (b) Elementary Reactions Important in Combustion [R] . Estler, R. C., Reisler, H., Wittig, C. 1981

机译：激光动力学光谱研究（a）硝基烷烃的单分子反应和（b）燃烧中重要的基本反应

From Umpolung to Alternation: Modified Reactivity of Donor-Acceptor Cyclopropanes Towards Nucleophiles in Reaction with Nitroalkanes

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