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通过NaN催化亚磷酸三烷基酯、芳基甲基亚甲基氰基乙酸乙酯和乙炔二羧酸二烷基酯之间的三组分反应高效合成膦酰化环戊烯酮。

An efficient synthesis of phosphonated cyclopentenones by NaN-catalyzed three-component reaction between trialkyl phosphites, ethyl arylmethylidenecyanoacetates and dialkyl acetylenedicarboxylates.

作者信息

Ranjbar Derranji Akram, Anary-Abbasinejad Mohammad

机构信息

Department of Chemistry, Faculty of Science, Vali-E-Asr University of Rafsanjan, Rafsanjan, 7718897111, Iran.

出版信息

Mol Divers. 2024 Feb;28(1):209-216. doi: 10.1007/s11030-023-10744-1. Epub 2023 Oct 16.

DOI:10.1007/s11030-023-10744-1
PMID:37843783
Abstract

NaN-catalysed three-component reaction between trialkyl phosphites, dialkyl acetylenedicarboxylates and ethyl arylmethylidenecyanoacetates afforded phosphonated cyclopentenone derivatives. The process involves one C-P and two C-C bond formations in one synthetic step. All reactions were conducted in acetone as solvent at room temperature and the products were obtained in high yields as stable solids. The products were isolated and purified by simple washing with water and diethyl ether without need to tedious chromatography methods. The structures of products were proved by H, C and P NMR and IR spectral and elemental analysis data.

摘要

NaN催化亚磷酸三烷基酯、乙炔二羧酸二烷基酯和芳基甲基亚甲基氰基乙酸乙酯之间的三组分反应,得到了膦酸化环戊烯酮衍生物。该过程在一个合成步骤中涉及一个C-P键和两个C-C键的形成。所有反应均在丙酮作为溶剂的条件下于室温进行,产物以高产率获得为稳定的固体。通过用水和乙醚简单洗涤即可分离和纯化产物,无需繁琐的色谱方法。产物的结构通过H、C和P NMR以及IR光谱和元素分析数据得以证实。

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本文引用的文献

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Phosphonates and Phosphonate Prodrugs in Medicinal Chemistry: Past Successes and Future Prospects.药物化学中的膦酸盐和膦酸盐前药:过去的成功与未来的前景
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Stereoselective NaN3-catalyzed halonitroaldol-type reaction of azetidine-2,3-diones in aqueous media.水相中氮杂环丁烷-2,3-二酮的立体选择性NaN₃催化卤代硝基醇型反应。
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