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Synthesis of new 2-aminobenzimidazole derivatives. Reaction of 2-arylideneaminobenzimidazole with selected nitriles containing active methylene group.

Anna Nowicka 1Wanda P. Nawrocka 1Hanna Liszkiewicz 1Andrzej Dryś 2

1. Akademia Medyczna, Katedra Technologii Leków, Nankiera 1, Wrocław 50-140, Poland
2. Medical University, Department of Phisical Chemistry (DPC), Nankiera 1, Wrocław 50140, Poland


Schiff bases 2-7 obtained from 2-aminobenzimidazole (1) with 2,3-dimethoxy-, 3,4-dimethoxy-, 4-methoxy-, 4-chloro-, 4-bromo- and 2-bromobenzaldehyde. A series of pyrimido[1,2-a]- benzimidazole and α-cyanocinnamic derivatives have been synthezied in the reactions of Schiff bases 2-7 with selected nitriles α-containing active methylene group: malononitrile 8-12, cyanoacetamide 13-16, benzoylacetonitrile 17-21, benzylonitrile 22-24, cyanoaceticmethyl ester 25-28 and cyanoacetic benzylamide 29 (Scheme 1). The structure 8-29 were confirmed by the results of elemental analysis and their IR, 1H-, 13C-NMR and MS spectra.

Ab initio geometry optimization calculations for three pairs 1H and 10H of possible products 10 and 10a, 17 and 17a, 24 and 24a was performed within the density functional theory (DFT). The computational study was performed using Gaussian 98 program. calculated energies for optimized structures are presented in Table 1. Energy differences ΔE suggest that 10, 17 and 24 are more propable products than corresponding structures 10a, 17a and 24a respectively.

The products 8-29 of various chemical structure were obtained, which are interest for biological studies or which can be substrates for further syntheses.


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Related papers

Presentation: Poster at VIII Multidyscyplinarna Konferencja Nauki o Leku, by Anna Nowicka
See On-line Journal of VIII Multidyscyplinarna Konferencja Nauki o Leku

Submitted: 2012-03-13 13:20
Revised:   2012-05-13 12:56