Cinchona alkaloids compound and preparation method thereof

A kind of technology of cinchonaine and compound, applied in the field of cinchonaline compound and preparation thereof

Inactive Publication Date: 2015-08-26
KUNMING UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] However, most of the structural modification of cinchona base is focused on the transformation of a certain group, such as the substitution reaction on the 9-hydroxyl group, the quaternization of the quinuclidine nitrogen atom, etc., but its skeleton structure is particularly Is the modification of quinucline rarely involved

Method used

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  • Cinchona alkaloids compound and preparation method thereof
  • Cinchona alkaloids compound and preparation method thereof
  • Cinchona alkaloids compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] Embodiment 1: the cinchona alkaloid compound of structural formula as shown in formula I:

[0016]

[0017] Wherein, R is 1.

[0018] The preparation method of above-mentioned compound is as follows:

[0019] Weigh 50 mg of quinidine (0.154 mmol, 1 eq) into a 25 mL single-necked bottle, add 10 mL of anhydrous acetonitrile to dissolve, then add 63.8 mg of potassium carbonate (0.46 mmol, 3 eq) to the solution, and place in an ice bath 116.7 mg (0.46 mmol, 3 eq) of iodine was added at the same time, and the mixture was stirred in an ice bath for 3 hours. After the reaction was detected by TLC, the reaction was quenched with aqueous sodium thiosulfite solution, and the aqueous phase was extracted three times with 30 mL of dichloromethane, and the combined organic phase, washed with water and saturated brine successively, dried over anhydrous magnesium sulfate, filtered, evaporated to dryness under reduced pressure, and purified by silica gel column chromatography (eluen...

Embodiment 2

[0020] Embodiment 2: the cinchona alkaloid compound of structural formula as shown in formula I:

[0021]

[0022] Wherein, R is 1.

[0023] The preparation method of above-mentioned compound is as follows:

[0024] Weigh 50 mg of quinidine (0.154 mmol, 1 eq) into a 25 mL single-necked bottle, add 10 mL of anhydrous acetonitrile to dissolve, then add 85.7 mg of potassium carbonate (0.62 mmol, 4 eq) to the solution, and place in an ice bath Add 157.4 mg iodine (0.62 mmol, 4eq), and stir the mixture under ice bath for 4 hours. After the reaction is detected by TLC, the reaction is quenched with aqueous sodium thiosulfite solution, and the aqueous phase is extracted 4 times with 30 mL dichloromethane, and the organic phases are combined , washed with water and saturated brine successively, dried over anhydrous magnesium sulfate, filtered, evaporated to dryness under reduced pressure, and purified by silica gel column chromatography (eluent: chloroform / methanol = 20 / 1, v / v) t...

Embodiment 3

[0025] Embodiment 3: the cinchona alkaloid compound of structural formula as shown in formula I:

[0026]

[0027] wherein R is H.

[0028] The preparation method of above-mentioned compound is as follows:

[0029] Weigh 50 mg (0.11 mmol, 1 eq) of the above compound A, place it in a 25 mL single-necked flask, add 10 mL of dry toluene to dissolve, slowly add 62 mg of tributyltin hydride (0.22 mmol, 2 eq) and azobisisobutyronitrile 7 mg (0.044 mmol, 0.4 eq), heated at 120°C for 24 hours under reflux, monitored by TLC, evaporated to dryness under reduced pressure, and purified by silica gel column chromatography (eluent: trichloro Methane / methanol = 4 / 1, v / v), and the light yellow solid was obtained as compound B ( figure 2 ).

[0030] Compound B can be used as the catalyst of N-Nitrosoaldol reaction, and specific examples are as follows:

[0031]

[0032] Add nitrosobenzene (107 mg, 1 mmol) to a 25 mL reaction vial, then add 4 mL of CHCl 3 , stirred well until disso...

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Abstract

The invention discloses a cinchona alkaloids compound with a new macrocyclic structure, and a preparation method thereof. The cinchona alkaloids compound is prepared with cinchona alkaloids quinidine as a substrate. According to the preparation method, quinidine is subjected to a halogen cyclization reaction, such that the new macrocyclic structure is obtained. Related derivatives can be obtained through the changes on the C11-locus. The cinchona alkaloids compound provided by the invention can be used as a novel chiral catalyst or a ligand. The preparation method is simple, and yield is high.

Description

technical field [0001] The invention belongs to the field of organic chemistry, and in particular relates to a cinchona alkaloid compound with a new macrocyclic structure and a preparation method thereof. Background technique [0002] Cinchona alkaloids are a class of natural alkaloids found in the bark and root bark of the cinchona tree, mainly including quinine, quinidine, cinchonine and cinchonine. Cinchonaine has important biological activities, such as anti-heat, anti-malarial, etc., and has been widely used. At the same time, cinchona base is used in various catalytic reactions, especially asymmetric catalysis, as an important catalyst and ligand in chemical synthesis. Due to the unique chiral molecular structure of this type of compound, various catalysts designed based on it have made outstanding achievements in the fields of chiral primary amine catalysis, thiourea catalysis, base catalysis and phase transfer catalysis in recent years. Progress. [0003] However,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D453/04C07D498/18
CPCC07D453/04C07D498/18
Inventor 廖霞俐张伟任玉峰杨健杨波
Owner KUNMING UNIV OF SCI & TECH
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