Reactions with 2-Aminobenzimidazole: Synthesis of Several New Pyrimido[1,2-a]benzimidazole Derivatives
β Scribed by Abdou O. Abdelhamid; Bahia Y. Riad; Suzan I. Aziz
- Publisher
- John Wiley and Sons
- Year
- 1987
- Tongue
- English
- Weight
- 223 KB
- Volume
- 320
- Category
- Article
- ISSN
- 0365-6233
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β¦ Synopsis
Several new pyrimido[ 1,2-albenzimidazole derivatives were synthesized by reacting 2-aminobenzimidazole with u, p-unsaturated nitriles and benzoylacetonitrile derivatives. The structures of the products were established on the basis of elemental analyses, IR and 'H-NMR spectral data.
Umsetzungen mit 2-Aminobenzimidazol: Synthese einiger neuer Pyrimidd 1,2-albenzimidazol-Derivate
Mehrere neue Pyrimidol1,2-albenzimidazole Derivate wurden durch Reaktionen von 2-Aminobenzimidazol mit u, P-ungesΓ€ttigten Nitrilen und Benzoyiacetonitril-Derivaten synthetisiert. Die Strukturen der neuen Derivate wurden anhand der Elementaranalyse, der IR-und 'H-NMR-Spectren identifiziert.
The incorporation of an imidazole nucleus, a biologically accepted pharmacophore, in the benzimidazole nucleus has made it a versatile heterocycle possessing a wide spectrum of biological activities. In addition, a large variety of substituted 2-aminobenzimidazoles have been found to possess in vivo and in vitro growth inhibitory activity against various strains of bacteria, fungi and viruses. Moreover, several 1and 1,3-disubstituted benzimidazoles and pyrimido[1,2-a]benzimidazoles are known to exhibit CNS depressant, anti-inflammatory, antithyroid and cardiovascular activitiesl). The above mentioned biological and medicinal activities of benzimidazoles and related compounds prompted our interest for the synthesis of severai new derivatives of these ring systems. The reactions of 2-aminobenzimidazole (1) with a, 0-unsaturated nitriles and benzoylacetonitrile derivatives (2) seemed to US to be a soie, easy and facile route for the synthesis of these derivatives.
π SIMILAR VOLUMES
Hydrazonoyl halides 4 react readily with either 3-amino-2,3-dihydro-6-methyl-2-thioxo-4(1H)-pyrimidinone 5 or 3-amino-6-methyl-2-methylthio-4(3H)-pyrimidinone 6 to form 6H-pyrimido [1,2-b][1,2,4,5]tetrazin-6-ones 9. The mechanism of the studied reactions is discussed.
Benzofuroylhydroxamoyl chloride (3) reacted with acrylonitrile, N-tolylmaleimide and active methylene compounds to afford the isoxazoline 4, the pyrrolidino13,4-d]isozazoline 5 and the isoxazole derivatives 6, 7, respectively. Nitrosoirnidazo[ 1,2-alpyridines 10 and the imidazo[ 1,2-alpyrimidine 12
Hydrazonoyl bromides 1a-c react with 5-amino-3phenyl-1H-pyrazole, 5-amino-1H-1,2,4-triazole, 2aminopyridine, 2-aminopyrimidine, and 2-aminobenzimidazole to afford the corresponding imidazo[1,2-b]pyrazoles 10, imidazo[1,2-b]-1,2,4-triazoles 11, imidazo[1,2-a]pyridines 16, imidazo[1,2-a]pyrimidines 17