Investigation of the synthesis of imidazole derivatives with (R)-(-)-(S)-(+)- mandelic acid under microwave and classical conditions and examination of their molecular recognition properties

Benzimidazole derivatives are at the forefront of research in Inorganic Chemistry, Pharmaceutical Chemistry and Biochemistry due to their broad pharmacological methods and diverse biological activites. As synthesis methods, both microwave assisted and classical methods were investigated. In this study, the aim was to synthesize benzimidazoles using (R)-(-)- Mandelic acid, 98 % and (S)-(+)- Mandelic acid, 98 %, as targets with o-phenylenediamine, 4-chloro-o-phenylenediamine and 4-bromo-o-penylenediamine as rectants respectively. Different benzimidazole compounds were synthesized using (R)-(-)-Mandelic acid, (S)-(+)-Mandelic acid and o-phenylenediamine derivatives via both microwave assisted and classical methods. In the synthesis carried out under classical conditions, it was obtained with 93 % yield in 24 hours at 70 oC, while the microwave method yielded 95 % 20 minutes at 700 watts and 80 oC, a relatively higher yield. The yield and reaction times obtained with both methods were quite good. Reactions crnied out using the microwave method were completed in a sharter time than the classical method and demonstrated the method's effectiveness with higher product yield. Furthermore, UV-Vis spectroscopic titration studies of the synthesized chiral benzimidazole derivative (R)-(1H-benzo[d]imidazole-2-yl)-1-phenylmethanol with (R)-(-)-a- methyl benzylamine were examined, UV-Vis analyses indicated that characteristic absorbance changes occurred during complex formation and that the interaction had a 1:1 stoichiometry in contrast, UV-Vis spectroscopic measurements between the two molecules. In contrast, UV-Vis spectroscopic measuremant between (R)-2-(4-bromo-benzo[d]imidazol-2-yl)-2-phenylmethanol and (R)-(-)-a-methyl benzylamine shawed that no significant binding or complex formation occured between the two molecules. The structure of the synthesized compounds was allucidated using methods such as 1HN-NMR, 13C-NMR and FT-IR. This research aims to evaluate alternative synthesis methods for benzimidazole derivatives and to contribute to understanding the effects of their chiral structures on biological interactions. Keywords: Mandelic acid, Imidazole, Benzimidazole, Microwave, UV-Vis