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IMIDAZOLE: SYNTHESIS, PROPERTIES AND BIOLOGICAL …
Considerable attention has been focused on the synthesis of benzimidazoles due to having a broad spectrum of biological activities such as anti-parasitic, fungicidal, anti-thelemintic and anti-inflammatory activities. As a part of our research work in this area, a series of benzimidasole derivatives (3a-n) were synthesized in good to high yields by reaction of o-phenylenediamine and different aromatic aldehydes in the presence of sodium hexafluroaluminate, Na3AlF6, as an efficient catalyst at 50 C. This environmentally benign and practical method offers several advantages, such as high yields, use of available catalyst, mild reaction conditions and easy workup. The antibacterial activity of these benzimidasoles was also evaluated using Staphylococcus aureus (mm) and Escherichia coli (mm) bacterial strain. All synthesized materials were characterized using IR and NMR spectroscopy as well as microanalyses data.
Benzimidazole and imidazole derivatives are very useful bioactive intermediates for the preparation of pharmalogical and biological active molecules (-). This ring system is present in numerous antiparasitic, fungicidal, antithelemintic and anti-inflammatory agents (-). There are two general methods for the synthesis of 2-substituted benzimidazoles (-). The most general method is a condensation reaction of o-phenylenediamine with carboxylic acids or their derivatives such as nitriles, imidates or ortho esters (), under strongly acid conditions or in combination with very high temperatures and/or microwave irradiations. The other one includes an oxidative cylocondensation reaction of Schiff bases in turns by condensation of o-phenylenediamine with aldehyde (, , ). A variety of oxidants and catalysts have been used for preparation of benzimidazoles. Although these methods worked nicely in many cases, however, some of these suffer from one or more limitations such as low yields, use of volatile or toxic organic solvents, requirement of excess amounts of catalysts or reagents, special apparatus and harsh reaction conditions. Consequently, development of convenient, high yield and environmentally benign procedure for synthesis of benzimidazoles is still a challenging research.
EINECS Numbers Database | Chemical Synthesis Database
Due to the important biological activity of benzimidazoles and in line with our research works in synthesis of this ring system (-) we wish to report a simple procedure for preparation of 2-arylbenzimidazoles through a condensation reaction of o-phenylenediamine and aromatic aldehydes in the presence of Na3AlF6 as a catalyst. We also report the antibacterial activity of these compounds.
Cyclohexyl bromide; Molecular Formula: C 6 H 11 Br
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