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Ivonin M. A., Krivenko A. P., Abdulhamid H. A., Krivenko A. P., Ivonin M. A., Sorokin V. V. Synthesis and Ways of Formation of Hydroxyphenyl Substituted Benz[4,5]imidazole-1,2,3,4,5,6- hexahydro[1,2-a]quinazolines. Izvestiya of Saratov University. New series. Series: Chemistry. Biology. Ecology, 2018, vol. 18, iss. 1, pp. 4-? DOI: https://doi.org/10.18500/1816-9775-2018-18-1-4-8


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Synthesis and Ways of Formation of Hydroxyphenyl Substituted Benz[4,5]imidazole-1,2,3,4,5,6- hexahydro[1,2-a]quinazolines

Abstract

To synthesize new potentially biologically active benzimidazoloquinazolines, a three-component condensation of 2-aminobenzimidazole, cyclohexanone and hydroxylatedbenzaldehydes was studied. The reaction proceeds regioselectively when the equimolar ratios of the reagents are boiled for 3 hours in N,N-dimethylformamide and is accompanied by the formation of ortho-phenyl substituted hexahydrobenz[4,5]imidazolo [1,2-a]quinazolines having an angular articulation of the rings and a different number and position of hydroxyl groups in the phenyl substituent. The peculiarity of the ortho-hydroxyphenyl-substituted product is the presence of an intramolecular hydrogen bond between the spatially approximated NH and OH groups, which is confirmed by the shift of the proton NH signal to a weak field in the 1H NMR spectrum and data obtained with the molecular mechanics method (MM2). The probable stadiality of the process is established by means of oncoming synthesis, the interaction of the previously synthesized aldimine (based on salicylaldehyde and 2-aminobenzimidazole) and cyclohexanone. The composition and structure of hydroxyphenyl-substituted benz[4,5]imidazolo-1,2,3,4,5,6-hexahydro[1,2-a] quinazolines was confirmed by elemental analysis and NMR 1H spectra in which there are singlets of methine protons H5 (6.22–6.59 ppm), NH protons (9.02–11.91 ppm), multiplets of alicyclic protons (1.08–2.54 ppm), benzene rings (6.54–7.28 ppm) and (7.10–8.18 ppm), hydroxyl groups (8.16–10.29 ppm).

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