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Synthesis method of novel thiazole ring derivative

A synthesis method and technology of thiazole rings, which are applied in the field of synthesis of new thiazole ring derivatives, can solve the problems of difficult control, severe reaction conditions, complicated operation, etc., and achieve high reaction yield and reduction of acidic and basic substances and metals The effect of using and reducing the discharge of three wastes and the pollution of the environment

Inactive Publication Date: 2018-01-09
HENAN NORMAL UNIV
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Problems solved by technology

[0003] Many methods for the synthesis of thiazole ring derivatives have been reported so far, the most classic of which is the use of α-bromoacetophenone as a raw material and thiourea in ethanol for the reflux reaction, in addition to benzoyl isosulfide Cyanate esters, secondary amines, and butynyl esters use enzyme-catalyzed one-pot methods to generate thiazole ring derivatives, and nano-chitosan and iodine-catalyzed conversion of acetophenone to thiazole rings, etc., but these methods generally have complex operations, Disadvantages such as severe reaction conditions and difficult control

Method used

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Examples

Experimental program
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Effect test

Embodiment 1

[0018] Synthesis of 2-amino-4-phenylthiazole

[0019] Add 3mL water into a 25mL reaction flask, then add 0.5mmol styrene, 1.25mmol K 2 S 2 o 8 and 1.25mmol KBr, reacted at 60°C for 12h, then added 0.5mmol thiourea, and continued to react at 60°C for 1h. After the reaction was completed, ethyl acetate was added for extraction, the organic phase was concentrated, and column chromatography gave 75mg of a white solid. The yield was 85%.

[0020] Product characterization: 1 H NMR (CDCl 3 ,600MHz)δ:7.81-7.75(m,2H),7.38(td,J=7.9,2.2Hz,2H),7.32-7.27(m,1H),6.72(d,J=2.4Hz,1H),5.29 (s,2H).

Embodiment 2

[0022] Synthesis of 2-amino-4-(p-bromophenyl)thiazole

[0023] Add 3mL water into a 25mL reaction flask, then add 0.5mmol p-bromostyrene, 1.25mmol K 2 S 2 o 8 and 1.25mmol KBr, reacted at 60°C for 12h, then added 0.5mmol thiourea, continued to react at 60°C for 1h, after the reaction was completed, added ethyl acetate for extraction, concentrated the organic phase, and obtained 105mg of white solid by column chromatography. The yield was 83%.

[0024] Product characterization: 1 H NMR (CDCl 3 ,600MHz):7.65(dt,J=8.4,1.6Hz,1H),7.50(dt,J=8.5,1.6Hz,1H),6.74(d,J=1.8Hz,1H),4.96(s,1H) .

Embodiment 3

[0026] Synthesis of 2-amino-4-(m-bromophenyl)thiazole

[0027] Add 3mL water to a 25mL reaction flask, then add 0.5mmol m-bromostyrene, 1.25mmol K 2 S 2 o 8 and 1.25mmol KBr, reacted at 60°C for 12h, then added 0.5mmol thiourea, continued to react at 60°C for 1h, after the reaction was completed, added ethyl acetate for extraction, concentrated the organic phase, and obtained 206mg of white solid by column chromatography. The yield was 81%.

[0028] Product characterization: 1H NMR (CDCl 3 ,600MHz):7.94(s,1H),7.68(d,J=7.8Hz,1H),7.41(d,J=7.9Hz,1H),7.23(t,J=8.0Hz,1H),6.74(s ,1H), 5.16(s,2H).

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Abstract

The invention discloses a synthesis method of a novel thiazole ring derivative, belonging to the technical field of organic synthesis. The synthesis method of the novel thiazole ring derivative comprises the steps of adding a styrene compound, potassium persulfate and potassium bromide into water in sequence, then reacting for 6-12 hours at 60 DEG C, adding a thiourea compound, and continuing to react for 1-2 hours at 60 DEG C, so as to prepare the target product thiazole ring derivative. The synthesis method has a high yield, is mild in reaction, is low-cost, and is environmentally friendly.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a method for synthesizing novel thiazole ring derivatives. Background technique [0002] Heterocyclic compounds widely exist in nature, accounting for about one-half of organic compounds. As a very important class of heterocyclic compounds, thiazole ring derivatives have good biological and pharmacological activities. They are also common heterocyclic compounds in natural products and medicines. They have significant antibacterial, anticancer and anti-inflammatory properties in medicine. Biological activity, widely used in the fields of pesticides and medicines, has become a hot spot in the research of green medicines in recent years. [0003] Many methods for the synthesis of thiazole ring derivatives have been reported so far, the most classic of which is the use of α-bromoacetophenone as a raw material and thiourea in ethanol for the reflux reaction. Cy...

Claims

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Application Information

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IPC IPC(8): C07D277/40
Inventor 马春华苗玉琪丁清杰毛龙飞田庆李伟
Owner HENAN NORMAL UNIV
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