Synthesis and chiral separation of atropisomers of 4,5-Di methyl increment 4 N-phenyl N-aryl imidazoline-2-thione derivatives

Synthesis of three chiral 4,5-Di methyl increment (4) N-phenyl N-aryl imidazole-2-thione derivatives was obtained by the condensation reaction of thiourea derivatives with alpha-hydroxy ketone. The structure of these compounds has been characterized by using spectroscopic methods (UV, IR, H-1 NMR, and C-13 NMR). The 4,5-Di methyl increment (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 (R) AD, Chiralcel (R) OD, Chiralcel (R) OD-H, Chiralcel (R) OJ, Chiralcel (R) OD-3R, Chiralcel (R) OZ-3, and Chiralpak (R) AS-3R. The impact of ortho-substituent in the resolution of 4,5-Di methyl increment (4) N-phenyl N-aryl imidazole-2-thione derivatives was also studied in this work.