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

Abstract

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, 1 H NMR, and 13 C 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.