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Enantioselective Amination of 4-Substituted Pyrazolones Catalyzed by Oxindole-Containing Thioureas and by a Recyclable Linear-Polymer-Supported Analogue in a Continuous Flow Process
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2023-12-14 , DOI: 10.1021/acs.joc.3c02069
Rodrigo Sánchez-Molpeceres 1 , Laura Martín 1 , Noelia Esteban 2 , Jesús A Miguel 2 , Alicia Maestro 1 , José M Andrés 1
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2023-12-14 , DOI: 10.1021/acs.joc.3c02069
Rodrigo Sánchez-Molpeceres 1 , Laura Martín 1 , Noelia Esteban 2 , Jesús A Miguel 2 , Alicia Maestro 1 , José M Andrés 1
Affiliation
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A highly efficient organocatalytic amination of 4-substituted pyrazolones with azodicarboxylates mediated by a novel quinine-derived thiourea with a 3,3-diaryl-oxindole scaffold is reported. This synthetic method furnished 4-amino-5-pyrazolones in high yields and with excellent enantioselectivities (up to 97:3 er) at room temperature in short reaction times. Moreover, a linear-polymer-supported bifunctional thiourea, synthesized by reacting a bifunctional aromatic monomer (biphenyl) with isatin in superacidic media and further derivatization, was proven to be also an efficient heterogeneous organocatalyst for this α-amination reaction. The practical value of this process was demonstrated by the use of the immobilized catalyst in recycling experiments, maintaining the activity without additional reactivation, and in flow processes, allowing the synthesis of 4-amino-pyrazolone derivatives in a gram scale with high yield and enantioselectivity.
中文翻译：
含羟吲哚硫脲和可回收线性聚合物支撑类似物在连续流动过程中催化 4-取代吡唑啉酮的对映选择性胺化
报道了一种新型奎宁衍生硫脲与 3,3-二芳基-羟吲哚支架介导的 4-取代吡唑啉酮与偶氮二羧酸盐的高效有机催化胺化。该合成方法在室温下、反应时间短的情况下以高产率和优异的对映选择性（高达 97:3 er）提供了 4-氨基-5-吡唑啉酮。此外，通过双官能芳香族单体（联苯）与靛红在超酸性介质中反应并进一步衍生化合成线性聚合物负载的双官能硫脲，被证明也是该α-胺化反应的有效多相有机催化剂。该方法的实用价值通过在回收实验中使用固定化催化剂来证明，无需额外的再活化即可保持活性，并且在流动过程中，可以以高收率和对映选择性合成克级的4-氨基-吡唑啉酮衍生物。
更新日期：2023-12-14
中文翻译：
含羟吲哚硫脲和可回收线性聚合物支撑类似物在连续流动过程中催化 4-取代吡唑啉酮的对映选择性胺化
报道了一种新型奎宁衍生硫脲与 3,3-二芳基-羟吲哚支架介导的 4-取代吡唑啉酮与偶氮二羧酸盐的高效有机催化胺化。该合成方法在室温下、反应时间短的情况下以高产率和优异的对映选择性（高达 97:3 er）提供了 4-氨基-5-吡唑啉酮。此外，通过双官能芳香族单体（联苯）与靛红在超酸性介质中反应并进一步衍生化合成线性聚合物负载的双官能硫脲，被证明也是该α-胺化反应的有效多相有机催化剂。该方法的实用价值通过在回收实验中使用固定化催化剂来证明，无需额外的再活化即可保持活性，并且在流动过程中，可以以高收率和对映选择性合成克级的4-氨基-吡唑啉酮衍生物。
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