Kotlyar V. Chalcones of the benzimidazole and imidazole series: synthesis and reactivity

Objects of study: Chalcones of benzimidazole and imidazole series. Aim: synthesis and study of the structure, acid-base and spectral properties of chalcones containing benzimidazole or imidazole substituents (chalcones analogs) and also 2 - pyrazoline, cyclopropanes and cyclic aziridinanils obtained from them. Methods and equipment: organic synthesis, elemental analysis, IR- and UV- absorption and emission spectroscopy, 1H NMR spectroscopy and chromato-mass spectrometry, quantum-chemical calculations. Theoretical and practical results: conditions for the synthesis of chalcones of benzimidazole and imidazole series have been optimized. For a desired oxidation of pyrazolines into pyrazoles two fairly universal systems have been proposed. The Corey reaction has been used for cyclopropanation of chalcones and tsianstirols of the benzimidazole series with the conservation of trans-placement of substituents in the three-member ring. Bromination of benzimidazole analogs of chalcones proceeds specifically to form monobromides or dibromide (for N-CH3 and NH derivatives respectively). Their further cyclocondensation with 1,2- diamines results in cyclic aziridinanils. The degree of implementation: the majority of the obtained compounds have been passed to the R&D Company "Ukrorgsintez" for the direct study of their biological activity or assessment as intermediates in the synthesis of required target compounds. The area of use: the elaboration of new methods and techniques for the synthesis of derivatives of benzimidazole and imidazole.