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Preparation method of 2-(2,6-dibenzoyl phenyl)thiazole-5-ethyl formate derivative

A technology of dibenzoyl phenyl and ethyl formate, which is applied in the field of preparation of 2-thiazole-5-ethyl formate derivatives, and can solve the problems of lack of new guiding groups and the like

Inactive Publication Date: 2014-06-18
CHINA PHARM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There is a lack of new directing groups with higher activity and easy modification or removal to guide the occurrence of diacylation reactions

Method used

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  • Preparation method of 2-(2,6-dibenzoyl phenyl)thiazole-5-ethyl formate derivative
  • Preparation method of 2-(2,6-dibenzoyl phenyl)thiazole-5-ethyl formate derivative
  • Preparation method of 2-(2,6-dibenzoyl phenyl)thiazole-5-ethyl formate derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] Ethyl 2-(2,6-dibenzoylphenyl)thiazole-5-carboxylate (1)

[0017]

[0018] Take a reaction tube, add substrate 0.5mmol and substituted benzaldehyde (3mmol, 6eq), diacetonitrile palladium chloride (6.5mg, 0.025mmol, 0.05eq), triphenylphosphine (13mg, 0.05mmol, 0.1eq), Trimethylacetic acid (0.115mL, 1mmol, 2eq), TBHP (65% solution) (0.3mL, 2mmol, 4eq), and o-dichlorobenzene 2mL were reacted in an oil bath at 160°C for 24 hours. The reaction system was cooled to room temperature, diluted with ethyl acetate, and filtered through celite to remove metal residues. The filtrate was subjected to saturated NaOH solution, saturated Na 2 SO 3 solution, washed with saturated brine, anhydrous Na 2 SO 4 Dry and concentrate under reduced pressure to obtain a dark crude product, which is then subjected to silica gel column chromatography to obtain 184 mg of a white solid product with a yield of 83.4%.

[0019] IR (KBr): 3481, 3416, 3134, 3098, 2360, 2331, 1711, 1671, 1587, 1449, ...

Embodiment 2

[0021] Ethyl 2-(2,6-di-p-chlorobenzoylphenyl)thiazole-5-carboxylate (2)

[0022]

[0023] Take a reaction tube, add substrate 0.5mmol and substituted benzaldehyde (3mmol, 6eq), diacetonitrile palladium chloride (6.5mg, 0.025mmol, 0.05eq), triphenylphosphine (13mg, 0.05mmol, 0.1eq), Trimethylacetic acid (0.115mL, 1mmol, 2eq), TBHP (65% solution) (0.3mL, 2mmol, 4eq), and o-dichlorobenzene 2mL were reacted in an oil bath at 160°C for 24 hours. The reaction system was cooled to room temperature, diluted with ethyl acetate, and filtered through celite to remove metal residues. The filtrate was subjected to saturated NaOH solution, saturated Na 2 SO 3 solution, washed with saturated brine, anhydrous Na 2 SO 4 Dry, concentrate under reduced pressure to obtain a dark crude product, and then obtain 175 mg of a white solid product through silica gel column chromatography, with a yield of 68.9%

[0024] IR (KBr): 3418, 3134, 2987, 1724, 1668, 1657, 1585, 1571, 1401, 1309, 1265, 1...

Embodiment 3

[0026] Ethyl 2-(2,6-di-m-chlorobenzoylphenyl)thiazole-5-carboxylate (3)

[0027]

[0028] Take a reaction tube, add substrate 0.5mmol and substituted benzaldehyde (3mmol, 6eq), diacetonitrile palladium chloride (6.5mg, 0.025mmol, 0.05eq), triphenylphosphine (13mg, 0.05mmol, 0.1eq), Trimethylacetic acid (0.115mL, 1mmol, 2eq), TBHP (65% solution) (0.3mL, 2mmol, 4eq), and o-dichlorobenzene 2mL were reacted in an oil bath at 160°C for 24 hours. The reaction system was cooled to room temperature, diluted with ethyl acetate, and filtered through celite to remove metal residues. The filtrate was subjected to saturated NaOH solution, saturated Na 2 SO 3 solution, washed with saturated brine, anhydrous Na 2 SO 4 Dry and concentrate under reduced pressure to obtain a dark crude product, which is then subjected to silica gel column chromatography to obtain 190 mg of a light yellow solid product with a yield of 74.6%.

[0029] IR (KBr): 3475, 3415, 3133, 2360, 2324, 1718, 1681, 16...

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Abstract

The invention relates to the field of organic chemistry, and particularly relates to a preparation method of a 2-(2,6-dibenzoyl phenyl)thiazole-5-ethyl formate derivative. The preparation method comprises the following step of synthesizing through free radical mechanism reaction under the condition of TBHP (T-Butyl Hydroperoxide) oxidation by taking a 2-phenyl thiazole-5-ethyl formate derivative and substituted benzaldehyde as substrates, diacetonitrile palladium chloride as a catalyst, triphenylphosphine as a ligand and trimethylacetic acid as an additive to obtain the 2-(2,6-dibenzoyl phenyl)thiazole-5-ethyl formate derivative. The synthetic method disclosed by the invention has the advantages of high yield, easiness for obtaining raw materials, simple reaction equipment, high atom economy and the like.

Description

technical field [0001] The invention relates to a preparation method of ethyl 2-(2,6-dibenzoylphenyl)thiazole-5-carboxylate derivatives, belonging to the field of organic chemistry synthesis methodology. Background technique [0002] The aryl ketone structure is an important class of synthetic intermediates, which are easy to be further functionalized, so they play an irreplaceable role in the synthesis of natural products and active compounds. The traditional Fried-Crafts acylation reaction requires stoichiometric acid chloride reagents, the reaction conditions are harsh and the regioselectivity is poor. Therefore, the transition metal-catalyzed coupling reaction of aldehydes and aromatic compounds has become an important method for the construction of aryl ketones in organic synthesis. [0003] Among them, the palladium-catalyzed cross dehydrogenation coupling reaction greatly realizes atom economy because none of the substrates needs to be preactivated. This kind of reac...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D277/56
CPCC07D277/56
Inventor 姚和权陈腾徐进宜吴晓明
Owner CHINA PHARM UNIV
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