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Method for preparing diindolylmethane compound
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A technology for diindolylmethane and compounds is applied in the field of preparing diindolylmethane compounds, and can solve the problems of long reaction time, heavy metal residue, excess catalyst and the like
Active Publication Date: 2014-06-25
TAIZHOU UNIV
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Problems solved by technology
In recent years, a lot of research has been done on the synthesis of diindolylmethane compounds, many synthetic methods have been explored, and many catalysts have emerged, such as: HBF 4 -SiO 2 ,ZnO,I 2 ,FeCl 3 ·6H 2 O,ZrCl 4 , CAN, RuCl 3 and LiClO 4 etc. Although these methods have all achieved certain success, there are some defects in them, such as: need excessive catalyst, long reaction time, harsh reaction conditions, use some toxic solvents, metal-containing catalysts in medical applications There is a heavy metal residue problem
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Embodiment 1
[0020] Add indole (5mmol), benzaldehyde (2.5mmol), and 0.5mmol ionic liquid into a 50mL single-necked bottle in turn, stir at room temperature for 10 minutes, TLC detection, the raw materials disappear, extract the reaction solution with ethyl acetate, combine the organic phase, and column The product was obtained by chromatographic separation with a yield of 90% and a content of 97%. 3,3'-(phenylmethylene)bis(1H-indole): 1 H NMR (400MHz, CDCl 3 )(ppm):7.93(s,2H),7.44-7.35(m,6H),7.31(t,J=4.3Hz,2H),7.26-7.15(m,3H),7.07-6.98(m,2H) ,6.75-6.58(m,2H),5.92(s,1H); 13 C NMR (100MHz, CDCl 3 )(ppm): 144.00, 136.70, 128.73, 128.22, 127.09, 126.14, 123.60, 121.93, 119.95, 119.75, 119.24, 111.01, 40.21.
Embodiment 2
[0022] Add indole (5mmol), 4-methylbenzaldehyde (2.5mmol), and 0.5mmol ionic liquid to a 50mL single-necked bottle in turn, stir at room temperature for 12 minutes, TLC detection, the raw materials disappeared, and the reaction solution was extracted with ethyl acetate, combined The organic phase was separated by column chromatography to obtain the product with a yield of 88% and a content of 95%. 3,3'-(p-tolylmethylene)bis(1H-indole): 1 H NMR (400MHz, CDCl 3 )(ppm):7.91(s,2H),7.43(d,J=8.0Hz,2H),7.37(d,J=8.1Hz,2H),7.26(d,J=8.0Hz,2H),7.22- 7.16(m,2H),7.11(d,J=7.9Hz,2H),7.06-7.00(m,2H),6.70-6.66(m,2H),5.88(s,1H),2.35(s,3H) .; 13 C NMR (100MHz, CDCl 3 )(ppm): 140.98, 136.70, 135.50, 128.92, 128.57, 127.12, 123.54, 121.89, 119.98, 119.94, 119.20, 110.99, 39.77, 21.09.
Embodiment 3
[0024] Add indole (5mmol), 4-methoxybenzaldehyde (2.5mmol), and 0.5mmol ionic liquid to a 50mL single-necked bottle in sequence, and stir at room temperature for 20 minutes. TLC detection shows that the raw materials disappear, and the reaction solution is extracted with ethyl acetate. The organic phases were combined and separated by column chromatography to obtain the product with a yield of 82% and a content of 93%. 3,3'-((4-methoxyphenyl)methylene)bis(1H-indole): 1 H NMR (400MHz, CDCl 3 )(ppm):7.92(s,2H),7.40(m,4H),7.29(d,J=2.0Hz,2H),7.22-7.13(m,2H),7.06-6.99(m,2H),6.88 -6.81(m,2H),6.67(d,J=1.5Hz,2H),5.87(s,1H),3.81(s,3H).; 13 C NMR (100MHz, CDCl 3 )(ppm): 157.93, 136.73, 136.25, 129.61, 127.09, 123.52, 121.90, 120.08, 120.00, 119.20, 113.59, 111.01, 55.22, 39.35.
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Abstract
The invention relates to an efficient and environment-friendly method for preparing a diindolylmethane compound by reacting indole and derivates with aldehyde and ketone under the catalyst and solvent-free mild room temperature reaction condition, the method comprises: by using the ionic liquid as a catalyst, catalyzing the indole and derivates with aldehyde and ketone under room temperature and normal pressure to obtain the corresponding diindolylmethane compound, the ionic liquid can be reused for five times and the reaction yield cannot be obviously reduced. The method is simple to operate, high in yield, good in reusability of catalytic reaction system, free from any organic solvent, mild in reaction condition, and good in industrial prospect.
Description
technical field [0001] The invention relates to a method for preparing diindolylmethane compounds by reacting indole and its derivatives with aldehydes and ketones under efficient, green and solvent-free conditions. technical background [0002] Diindolylmethane compounds have important biological and pharmacological activities and are widely used in the field of medicine. In recent years, a lot of research has been done on the synthesis of diindolylmethane compounds, many synthetic methods have been explored, and many catalysts have emerged, such as: HBF 4 -SiO 2 ,ZnO,I 2 ,FeCl 3 ·6H 2 O,ZrCl 4 ,CAN,RuCl 3 and LiClO 4 etc. Although these methods have all achieved certain success, there are some defects in them, such as: need excessive catalyst, long reaction time, harsh reaction conditions, use some toxic solvents, metal-containing catalysts in medical applications There is a heavy metal residue problem. Therefore, the development of efficient and green synthesis m...
Claims
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