Synthesis and structural investigation of some 1,4-disubstituted-2-pyrrolidinones
Synthesis and structural investigation of some 1,4-disubstituted-2-pyrrolidinones
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DOI：
10.3998/ark.5550190.0007.206
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发表时间：
2006-01-01
期刊：
影响因子：
0.9
通讯作者：
Mikulskiene, G
中科院分区：
文献类型：
--
作者：
Brokaite, K;Mickevicius, V;Mikulskiene, G
以1-芳基-4-肼羰基-2-吡咯烷酮为原料，与芳香醛、丙酮、2-丁酮和2,4-戊二酮缩合，合成了一系列1,4-二取代2-吡咯烷酮。由于分子中含有酰胺和亚甲基结构单元，大多数反应产物具有同分异构体。计算机分子模型被用来研究每个异构体的个体特征。根据分子模型的理论特征，通过IR、mass、H-1和C-13 NMR对合成化合物的结构进行了明确的分析。在这项工作中，所研究的化合物3-9的核磁共振光谱显示了一个成功的代表性例子的选择，并很好地支持了在不同极性的溶剂中，在亚甲基碎片中存在E/ z构型而形成的s-顺式和s-转换异构体的特性的解释。给出了完整的核磁共振分配数据。
A series of 1,4-disubstituted 2-pyrrolidinones was synthesized by condensation of 1-aryl-4-hydrazinecarbonyl-2-pyrrolidinones with aromatic aldehydes, acetone, 2-butanone, and 2,4-pentane-dione. Most of the reaction products have isomers owing to the amide and azomethine structural units in their molecules. Computer molecular modeling was used to study individual features of each isomer. The structures of the synthesized compounds were unambiguously elucidated by combining IR, mass, H-1, and C-13 NMR spectroscopy on the basis of the theoretical characteristics derived from molecular modeling. In this work the NMR spectra of the studied compounds 3-9 revealed a successful choice of the representative examples and good support for the explication of the peculiarities of s-cis and s-transisomers formed in amides by the existence of E/Z-configurations in azomethine fragments using solvents of different polarity. Data for the complete NMR assignments are presented.