63330-81-4Relevant academic research and scientific papers
Synthesis and biological evaluation of some novel-3-(5-substituted benzimidazol-2-yl)-5-arylisoxazolines
Reddy, Vanga Malla,Reddy, Kunduru Ravinder
, p. 1145 - 1148 (2011/10/08)
The synthesis of a new series of 3-(5-substituted benzimidazol-2-yl)-5-arylisoxazolines (6a-h) was achieved in excellent yields by the condensation of 1-(1H-benzimidazol-2-yl)-3-(substituted phenyl)prop-2-en-1-ones (5a-h) with hydroxylamine at room temperature. These 1-(1H-benzimidazol-2-yl)-3-(substituted phenyl)prop-2-en-1-ones (5a-h) were obtained by the condensation of 2-acetyl benzimidazoles (4a-d) with different aromatic aldehydes, which in turn were obtained by the oxidation of 2-(α-hydroxy)ethyl benzimidazoles (3a-d) prepared by the reaction of o-phenylenediamines (1a-d) with α-hydroxy propionic acid 2. The synthesized compounds were characterized by their IR, 1H NMR and MS analyses. These compounds were screened for their antibacterial and antifungal activity by standard methods and found some of them active.
Facile synthesis of alkoxyphthalimide derivatized benzimidazole assembled pyrazoles, pyrimidines and isoxazoles, via common intermediate chalcone
Bapna, Archita,Ojha, Swati,Talesara
, p. 1096 - 1107 (2008/12/23)
In the present investigation, synthesis of 2-(3-aryl-2-phenyl-3,4- dihydropyrazol-5-yl)-1-N-alkoxyphthalimidobenzimidazole 9a-h, 4-(1-N-alkoxyphthalimidobenzimidazol-2-yl)-6-arylpyrimidin-2-amine 10a-h and 2-(5-aryl-4,5-dihydroisoxazol-3-yl)-1-N-alkoxyphthalimidobenzimidazole 11a-h are described. Mild dichromate oxidation of 1-benzimidazol-2-yl-ethanol 1 gives 1-benzimidazol-2-yl-ethanone 2 which on Clasien condensation with various aromatic aldehydes yields the corresponding 3-aryl-1-(benzimidazol-2-yl)-prop-2- en-1-one 3a-d derivatives. Compound 3a-d act as key intermediates for all the three series of final compounds. In one pathway 3a-d is converted to its alkoxyphthalimide derivatives 5a-h by condensation with ω- bromoalkoxyphthalimides 4a-b, which cyclize with PhNHNH2/pyridine, guanidine nitrate/10% NaOH and hydroxylamine hydrochloride/CH3COOH to give 9a-h, 10a-h and 11a-h respectively. In an alternative route, reaction of 3a-d with all the three reagents affords 2-(3-aryl-2-phenyl-3,4-dihydropyrazol- 5-yl)benzimidazole 6a-d, 4-(benzimidazol-2-yl)-6-arylpyrimidin-2-amine 7a-d and 2-(5-aryl-4,5-dihydroisoxazol-3-yl)benzimidazole 8a-d which on condensation with co-bromoalkoxyphthalimides 4a-b give the final compounds 9a-h, 10a-h and 11a-h. Structure elucidations of all the compounds have been accomplished by elemental analysis, IR, 1H NMR and mass spectral data.
