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Synthesis of Alkyl Thiochromano[2,3-c]pyrrole-9-carboxylate Derivatives Utilizing Benzo[b]thiofuran-2,3-dione, Maleimides, and Alkyl Alcohol/Water Mixtures
Synthesis ( IF 2.6 ) Pub Date : 2024-02-22 , DOI: 10.1055/a-2260-0420
Jalal A. Zahra 1 , Mustafa M. El-Abadelah 1 , Mohammed M. Abadleh 2 , Salim S. Sabri 1 , Rania R. Abuzaid 1 , Dieter Schollmeyer 3
Affiliation  

A set of thiochromano[2,3-c]pyrrolidine-1,3-diones, incorporating α-hydroxy esters and their acids at the C-9 position, was prepared via direct interaction involving benzo[b]thiofuran-2,3-diones, maleimides, and alkyl alcohols in water at 90 °C. Structures of the new products were deduced from HRMS and NMR spectral data and confirmed by single-crystal X-ray crystallography. An insight into a proposed pathway involving a sequential Michael conjugate addition (initiated by the sulfur atom) and an aldol-type reaction is presented.



中文翻译:

利用苯并[b]噻喃-2,3-二酮、马来酰亚胺和烷基醇/水混合物合成烷基硫代苯并[2,3-c]吡咯-9-羧酸酯衍生物

一组硫代苯并[2,3- c ]吡咯烷-1,3-二酮,在C-9位置掺入α-羟基酯及其酸,通过涉及苯并[ b ]硫代呋喃-2,3-的直接相互作用制备二酮、马来酰亚胺和烷基醇在 90 °C 的水中。新产品的结构由 HRMS 和 NMR 光谱数据推导出来,并通过单晶 X 射线晶体学证实。深入探讨了涉及连续迈克尔共轭加成(由硫原子引发)和羟醛型反应的拟议途径。

更新日期:2024-02-23
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