Research in the field of imidazo[1,2-a]benzimidazole derivatives: XXVII. 1-acylmethyl-2-(ω-hydroxyalkylamino)-benzimidazoles and their transformation into derivatives of tricyclic systems

Abstract

1-Acylmethyl-2-(ω-hydroxyalkylamino)benzimidazoles were synthesized and their behavior under various conditions was investigated: at the thermolysis without solvent, at heating in DMF or in 2-aminoethanol, hydrohalic acids, and acetic anhydride, in the presence of chlorinating agents (SOCl 2 , POCl 3 ). Depending on the reaction conditions derivatives were obtained of 1H-imidazo[1,2-a]-benzimidazole, 9H-2,3-dihydroimidazo[1,2-a]benzimidazole, and 10H-2,3,4,10-tetrahydropyrimido[1,2-a]-benzimidazole that were suitable synthons for the synthesis of functionally substituted derivatives of these tricyclic systems.

Imidazo[1,2-a]benzimidazole derivatives: XXVIII. Syntheses and heterocyclizations on the basis of 1-allyl-2-aminobenzimidazole

“…The eluate was evaporated to obtain white crystalline product which was a mixture of cis and trans isomers of 1-(prop-2-en-1-yl)benzimidazol-2-amine V and VI and compound VII at a ratio of 2 : 9 : 9. Yield 0.9 g. 1 …”

“…IR spectrum, ν, cm -1 : 3445, 3335 (NH 2 ); 1630 (C=N) 1. H NMR spectrum (DMSO-d 6 ), δ, ppm: 4.57d (2H, NCH 2 , J = 4.8 Hz), 5.00-5.20 m (2H, CH 2 ), 5.80-5.97 m (1H, CH), 6.20 s (2H, NH 2 ), 6.75-7.18 m (4H, H arom ).…”

A Palladium Iodide-Catalyzed Oxidative Aminocarbonylation–Heterocyclization Approach to Functionalized Benzimidazoimidazoles

“…1 H -Benzo­[ d ]­imidazo­[1,2- a ]­imidazoles are an important class of polyheterocyclic derivatives, which display a wide range of pharmacological properties, including analgesic, anti-inflammatory, hypotensive, antiaggregant, hypoglycemic, and anticancer activities . Although several methods for the preparation of these compounds are currently known, the possibility to obtain functionalized 1 H -benzo­[ d ]­imidazo­[1,2- a ]­imidazole derivatives in one step by a catalytic multicomponent approach, starting from simple and/or readily available building blocks, is still of high synthetic interest.…”