铜催化的吡唑磺酰胺化学选择性合成：溶剂对硝基吡唑反应活性的影响

IF 2.5 3区化学 Q2 CHEMISTRY, ORGANIC

European Journal of Organic Chemistry Pub Date : 2024-10-21 DOI:10.1002/ejoc.202401097

Subhendu Bhowmik, RANA SAHA, Swarnendu Dutta, Arka Das, Rajarshi Jana, Krutika Sonar, Sreya Gupta

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引用次数: 0

摘要

摘要：本研究提出了一种铜催化、依赖溶剂的方法，用于在微波条件下直接从硝基吡唑和磺酰肼快速高效地合成 N-吡唑磺酰胺。该反应在吡唑的反应活性方面表现出明显的溶剂效应。离子液体 DBU-AcOH 触发了 4-硝基吡唑的反应，而在 PEG 中的反应则选择性地在吡唑的 3-amp; 5-位进行。该方法的主要应用包括以克为单位合成吡唑磺酰胺、磺胺苯并唑类似物和磺酰胺。

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Copper-Catalyzed Chemoselective Synthesis of Pyrazolo-Sulfonamide: Impact of Solvent on Nitro-pyrazole Reactivity

Abstract: This study presents a copper-catalyzed, solvent-dependent method for the rapid and efficient synthesis of N-pyrazolo-sulfonamides directly from nitro-pyrazole and sulfonyl hydrazide under microwave conditions. The reaction exhibits notable solvent effects in pyrazole’s reactivity. The ionic liquid DBU-AcOH triggered the reactivity of 4-nitro-pyrazole, whereas the reaction in PEG proceeded selectively at the 3- & 5-positions of pyrazole. Key applications of this method include the gram-scale synthesis of pyrazolo-sulfonamide, sulfaphenazole analogue and sulfonamide

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来源期刊

European Journal of Organic Chemistry 化学-有机化学

CiteScore

5.40

自引率

3.60%

发文量

752

审稿时长

1 months

期刊介绍： The European Journal of Organic Chemistry (2019 ISI Impact Factor 2.889) publishes Full Papers, Communications, and Minireviews from the entire spectrum of synthetic organic, bioorganic and physical-organic chemistry. It is published on behalf of Chemistry Europe, an association of 16 European chemical societies. The following journals have been merged to form two leading journals, the European Journal of Organic Chemistry and the European Journal of Inorganic Chemistry: Liebigs Annalen Bulletin des Sociétés Chimiques Belges Bulletin de la Société Chimique de France Gazzetta Chimica Italiana Recueil des Travaux Chimiques des Pays-Bas Anales de Química Chimika Chronika Revista Portuguesa de Química ACH—Models in Chemistry Polish Journal of Chemistry.