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With ammonium acetate; acetic acid; for 2h;Reflux;
General procedure: Aryl acetonitrile (3.2 mmol, 1.0 eq.), aldehyde (3.2 mmol, 1.0 equiv), and ammonium acetate (9.5 mmol, equiv) were mixed in glacial acetic acid (10 mL) and heated at reflux for 2 h. Following, the reaction mixture was cooled to room temperature. The precipitate that formed was collected by filtration, washed with water, followed by a small volume of methanol, and dried in a vacuum oven at 50 C for 18 h.
ethyl 4-cyano-1-(4-fluorophenyl)benzo[4,5]imidazo[1,2-a]pyridine-3-carboxylate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
80%
With piperidine; In ethanol;Reflux;
General procedure: A mixture of 2-(1H-benzo[d]imidazol-2-yl)acetonitrile (1) (1 mmol), ethyl 2,4-dioxo-4-arylbutanoate 2 (1 mmol), and piperidine (0.5 mmol) in EtOH (8 mL)was heated at reflux for 25-45 min. After completion of the reaction(monitored by TLC), the mixture was cooled to room temperature, and pure product 3 was obtained as yellow crystals. The product was isolated by filtration and oven-dried at 50-60 C.
2-(1H-benzimidazol-2-yl)-3-[4-(dimethylamino)-2-hydroxyphenyl]acrylonitrile[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
20%
With piperazine; In ethanol; for 4h;Reflux;
General procedure: To the solution of 2-(1H-benzimidazol-2-yl)acetonitrile (80 mg, 0.51 mmol), 4-methylbenzaldehyde (60 mg, 0.50 mmol) in ethanol (1.5 mL) was added 1,4-diazacyclohexane (45 mg, 0.52 mmol). The mixture was refluxed for 4 h in room temperature. The crude product was filtered off and purified by silica gel chromatography using cyclohexane-acetone-ethyl acetate (10:1:1) as eluant to afford compound 6 (120 mg, 93%).
4- (diphenylamino) benzaldehyde (20mmol), 2- benzothiazoleacetonitrile (20mmol) and anhydrous piperazine (4mmol) were dissolved in a solvent (42g) and heating-stirring was carriedout for 6 hours at 60 . Aftercooling, the precipitated solid was separated by filtration, and wasrecrystallized from again dimethylacetamide / chloroform / ethanol, andthen compound No. 3 (14.8mmol) was obtained. It was confirmed by variousanalysis that the obtained crystal is the desired product (Compound No.3). Theresults are shown in Table [1] to [Table 4].Using a corresponding aldehyde compound and an active methylene compound, to synthesize a compound according to [Table 1] in the same manner as in Synthesis Example 1. Synthesis results and a variety of analytical results are shown in Table 1] to [Table 4].
With sodium methylate; In acetonitrile; at 35℃; for 12h;Inert atmosphere;
Add compound II, compound III and sodium methoxide to acetonitrile under the protection of an inert gas (nitrogen)The ratio of the amount of the compound II, the compound III, and the sodium methoxide substance in the solvent is 1: 1.2: 0.2,Compound II was 1 mmol, the amount of acetonitrile was 10 mL, and the reaction was stirred at 35 C for 12 hours.The reaction was concentrated under reduced pressure, and purified by silica column chromatography using ethyl acetate / petroleum ether (v / v, 1: 5) to obtain the probe (I) (yield 60%).