Efficient synthesis method for imidazo indolone condensed heterocycle
A synthetic method and technology of fused heterocycles, which is applied in the field of synthesis of three types of fused heterocycles, can solve the problem that the expansion of substrates has not been further studied, and achieve the effect of mild reaction conditions
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Embodiment 1
[0021] In the Schlenk reaction tube, add o-fluorobenzaldehyde (0.5mmol), benzimidazole (0.5mmol), FeCl 3 ·6H 2 O (8mg, 0.05mmol), potassium phosphate (212mg, 0.1mmol) and DMF (2mL), the reaction tube was sealed, under air atmosphere, 110 ° C, reacted for 15 hours, after the reaction was completed, dichloromethane extracted three times, the organic layer Then washed three times with saturated brine, the organic layer was dried over anhydrous sodium sulfate, concentrated under reduced pressure, separated and purified by column chromatography to obtain product 1, its structure and characterization data are as follows:
[0022]
[0023] 11H-indolo[1,2-a]benzimidazol-11-one(1).an orange solid(103.4mg,97%),mp:232-234℃; 1 H NMR (500MHz, CDCl 3 / TMS): δ7.91(d, J=8.5Hz, 1H), 7.71(dd, J 1 =1.0Hz,J 2 =7.5Hz,1H),7.63-7.60(m,2H),7.62-7.49(m,1H),7.38-7.33(m,2H),7.26-7.21(m,1H)ppm. 13 C NMR (125MHz, CDCl 3 / TMS): 179.8, 149.1, 148.9, 143.3, 136.7, 130.0, 129.9, 127.9, 127.5, 125.9, ...
Embodiment 2
[0025] In a Schlenk reaction tube, add 4-bromo-2-fluorobenzaldehyde (0.5 mmol), benzimidazole (0.5 mmol), FeCl 3 ·6H 2 O (8mg, 0.05mmol), potassium phosphate (212mg, 0.1mmol) and DMF (2mL), the reaction tube was sealed, under air atmosphere, 110 ° C, reacted for 15 hours, after the reaction was completed, dichloromethane extracted three times, the organic layer Then washed three times with saturated brine, the organic layer was dried over anhydrous sodium sulfate, concentrated under reduced pressure, separated and purified by column chromatography to obtain product 2, its structure and characterization data are as follows:
[0026]
[0027] 3-bromo-11H-indolo[1,2-a]benzimidazol-11-one(2).an orange solid(127.1mg,85%),mp:219-221℃; 1 H NMR (500MHz, CDCl 3 / TMS): δ7.92(d,J=8.5Hz,1H),7.60-7.51(m,4H),7.40-7.36(m,2H)ppm. 13 C NMR (125MHz, CDCl 3 / TMS):178.6,149.0,148.9,143.9,131.3,129.7,129.0,128.3,126.8,126.2,124.8,124.2,115.3,111.1ppm.HRMS(ESI)m / z calcd for C 14 h 7 BrN 2...
Embodiment 3
[0029] In a Schlenk reaction tube, add 4-chloro-2-fluorobenzaldehyde (0.5 mmol), benzimidazole (0.5 mmol), FeCl 3 ·6H 2 O (8mg, 0.05mmol), potassium phosphate (212mg, 0.1mmol) and DMF (2mL), the reaction tube was sealed, under air atmosphere, 110 ° C, reacted for 15 hours, after the reaction was completed, dichloromethane extracted three times, the organic layer Then washed three times with saturated brine, the organic layer was dried over anhydrous sodium sulfate, concentrated under reduced pressure, separated and purified by column chromatography to obtain product 3, its structure and characterization data are as follows:
[0030]
[0031]3-chloro-11H-indolo[1,2-a]benzimidazol-11-one(3).an orange solid(103.2mg,81%),mp:242-244℃; 1 H NMR (500MHz, CDCl 3 / TMS): δ7.92(d, J=9.0Hz, 1H), 7.65(d, J=13.0Hz, 1H), 7.59(d, J=8.5Hz, 1H), 7.54-7.51(m, 1H) ,7.39-7.35(m,2H),7.21(dd,J 1 =2.0Hz,J 2 =8.0Hz,1H)ppm. 13 C NMR (125MHz, CDCl 3 / TMS):178.4,149.1,148.9,144.0,142.9,129.8,128...
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