Preparation method of tri-substituted oxazole derivatives with 2-site ester substitution

A derivative and tri-substitution technology, which is applied in the field of preparation of tri-substituted oxazole derivatives, achieves the effects of mild reaction conditions, wide substrate range and high yield

Inactive Publication Date: 2018-02-23
HUAQIAO UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although there are many traditional synthesis methods, in terms of the obtained products, the 2-position is an ester group-substituted oxazole synthesis method is seldom (the 2-position carboxyl-substituted oxazole can be obtained by unsubstituted oxazole and carbon dioxide under the catalysis of gold, Then obtain ester group substituted oxazole by esterification), and consult literature to know that one-step synthesis comprises the trisubstituted oxazole that 2-position ester group replaces is not

Method used

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  • Preparation method of tri-substituted oxazole derivatives with 2-site ester substitution
  • Preparation method of tri-substituted oxazole derivatives with 2-site ester substitution
  • Preparation method of tri-substituted oxazole derivatives with 2-site ester substitution

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Preparation of 2-carboxyethyl-4-benzoyl-5-phenyloxazole

[0029]

[0030] Add 0.2mmol of 1,3-diphenyl-3-glycine ethyl-2-alkene-1-one, 0.4mmol of iodine, 0.4mmol of potassium carbonate, 1mL of 1,2-dichloroethane and 1mL of toluene into a 25mL In the reaction tube, replace the gas in the reaction tube with oxygen, react at 80°C for 4 hours; add an appropriate amount of water or sodium chloride solution to stop the reaction, and cool to room temperature. The reaction solution was diluted with ethyl acetate, washed three times with water, and the organic phase was washed with anhydrous Na 2 SO 4 It was dried, filtered, concentrated, and the target product was purified by column chromatography (silica gel, 5% ethyl acetate / petroleum ether). The compound was characterized as follows: pale yellow solid; yield: (46mg, 72%); m.p.116-119°C; 1 HNMR (400MHz, CDCl 3 )δ 8.03-7.92(m, 4H), 7.64-7.58(m, 1H), 7.48(t, J=7.7Hz, 2H), 7.44-7.36(m, 3H), 4.55(q, J=7.1Hz, 2H), 1.47(t, J...

Embodiment 2

[0032] Preparation of 2-carboxyethyl-4-(4-methylbenzoyl)-5-phenyloxazole

[0033]

[0034] 0.2mmol of 1-(4-methylphenyl)-3-phenyl-3-glycinate ethyl-2-alkene-1-one, 0.4mmol of iodine, 0.4mmol of potassium carbonate, 1,2-dichloroethyl Add 1mL of alkane and 1mL of toluene into a 25mL reaction tube, replace the gas in the reaction tube with oxygen, and react at 80°C for 4h; add an appropriate amount of water or sodium chloride solution to stop the reaction, and cool to room temperature. The reaction solution was diluted with ethyl acetate, washed three times with water, and the organic phase was washed with anhydrous Na 2 SO 4 It was dried, filtered, concentrated, and the target product was purified by column chromatography (silica gel, 5% ethyl acetate / petroleum ether). The compound is characterized as follows: white solid; yield: (43mg, 64%); m.p.100-101°C; 1 HNMR (400MHz, CDCl 3 )δ 8.05-7.94 (m, 2H), 7.87 (d, J = 8.2Hz, 2H), 7.45-7.36 (m, 3H), 7.27 (d, J = 8.3Hz, 2H), 4....

Embodiment 3

[0036] Preparation of 2-carboxyethyl-4-(4-chlorobenzoyl)-5-phenyloxazole

[0037]

[0038] 0.2mmol of 1-(4-chlorophenyl)-3-phenyl-3-glycine ethyl-2-alkene-1-one, 0.4mmol of iodine, 0.4mmol of potassium carbonate, 1,2-dichloroethane Add 1mL and 1mL of toluene into a 25mL reaction tube, replace the gas in the reaction tube with oxygen, and react at 80°C for 4h; add an appropriate amount of water or sodium chloride solution to stop the reaction, and cool to room temperature. The reaction solution was diluted with ethyl acetate, washed three times with water, and the organic phase was washed with anhydrous Na 2 SO 4 It was dried, filtered, concentrated, and the target product was purified by column chromatography (silica gel, 5% ethyl acetate / petroleum ether). The compound is characterized as follows: white solid; yield: (45mg, 63%); m.p.120-123°C; 1 H NMR (400MHz, CDCl 3 )δ 8.05-7.97(m, 2H), 7.96-7.88(m, 2H), 7.50-7.38(m, 5H), 4.55(q, J=7.1Hz, 2H), 1.47(t, J=7.1Hz, 3H); 1...

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Abstract

The invention discloses a method for preparing a trisubstituted oxazole derivative substituted with a 2-position ester group. The specific reaction equation is as follows: the invention can synthesize a trisubstituted oxazole derivative with a 2-position ester group substitution which is not easily obtained by other methods .

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a preparation method of a trisubstituted oxazole derivative substituted with a 2-position ester group. Background technique [0002] Oxazole derivatives are a class of important heterocyclic compounds containing nitrogen and oxygen, which have a wide range of pharmaceutical activities, and have important application values ​​in anti-cancer, anti-inflammatory, anti-tumor, hypoglycemic and blood lipid drugs. Therefore, the research on new synthetic methods of oxazole compounds and their derivatives has important application value, and has attracted the attention of scientific researchers in related fields. [0003] The traditional synthesis methods of polysubstituted oxazoles include: dehydration cyclization of acyclic precursors, oxidative coupling of amines and aldehydes and ketones, oxidation of oxazolines and modification of oxazole rings, etc. Although t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D263/34C07D409/06
CPCC07D263/34C07D409/06
Inventor 程国林翁云翔
Owner HUAQIAO UNIVERSITY
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