Synthesis and chiral separation of atropisomers of 4,5‐Di methyl ∆4 N‐phenyl N‐aryl imidazoline‐2‐thione derivatives,Chirality

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Synthesis and chiral separation of atropisomers of 4,5‐Di methyl ∆4 N‐phenyl N‐aryl imidazoline‐2‐thione derivatives
Chirality ( IF 2.8 ) Pub Date : 2021-03-26 , DOI: 10.1002/chir.23306
Aicha Laoufi _{1,

2} , Nasser Belboukhari ₁ , Khaled Sekkoum ₁ , Hassan Y. Aboul-Enein ₃

Affiliation

Synthesis of three chiral 4,5‐Di methyl ∆⁴ N‐phenyl N‐aryl imidazole‐2‐thione derivatives was obtained by the condensation reaction of thiourea derivatives with α‐hydroxy ketone. The structure of these compounds has been characterized by using spectroscopic methods (UV, IR, ¹H NMR, and ¹³C NMR). The 4,5‐Di methyl ∆⁴ N‐phenyl N‐aryl imidazole‐2‐thiones display a chiral axis around the N‐C bond linking between the nitrogen of the heterocyclic framework and the carbon of the aryl group. Screening on chiral analysis of the atropisomers of these derivatives was performed by high‐performance liquid chromatography method on seven chiral selectors based on polysaccharides consisting of amylose and cellulose, namely, Chiralpak®AD, Chiralcel® OD, Chiralcel® OD‐H, Chiralcel® OJ, Chiralcel® OD‐3R, Chiralcel® OZ‐3, and Chiralpak® AS‐3R. The impact of ortho‐substituent in the resolution of 4,5‐Di methyl ∆⁴ N‐phenyl N‐aryl imidazole‐2‐thione derivatives was also studied in this work.

中文翻译：

4,5-二甲基∆4 N-苯基N-芳基咪唑啉-2-硫酮衍生物的阻转异构体的合成和手性分离

通过硫脲衍生物与α-羟基酮的缩合反应，可以合成三种手性4,5-Di甲基∆ ⁴ N-苯基N-芳基咪唑-2-硫酮衍生物。这些化合物的结构已通过使用光谱法（UV，IR，¹ H NMR和¹³ C NMR）进行了表征。4,5-二甲基∆ ⁴N-苯基N-芳基咪唑-2-硫酮在杂环骨架的氮与芳基碳原子之间的N-C键周围显示手性轴。通过高效液相色谱法，对基于直链淀粉和纤维素的多糖组成的七个手性选择剂，即Chiralpak®AD，Chiralcel®OD，Chiralcel®OD-H，Chiralcel®，通过高效液相色谱法对这些衍生物的阻转异构体进行手性分析筛选OJ，Chiralcel®OD-3R，Chiralcel®OZ-3和Chiralpak®AS-3R。在这项工作中，还研究了邻位取代基对4,5-Di甲基∆ ⁴ N-苯基N-芳基咪唑-2-硫酮衍生物的拆分的影响。

更新日期：2021-05-06

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