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Imidazo-[1,2-c]-quinazolin-3(2H)-one fused-heterocycle compounds and preparation method thereof

A compound, 2-c technology, applied in the direction of organic chemistry, can solve the problems of low yield and limited application, and achieve the effect of easy to obtain raw materials, convenient operation and easy control

Active Publication Date: 2015-03-25
ASSET SUZHOU PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The above shortcomings (three-step or four-step reaction, phosphorus-containing reagents, high temperature and multiple separation and purification, low yield, etc.) limit the application of many such compounds in practical research

Method used

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  • Imidazo-[1,2-c]-quinazolin-3(2H)-one fused-heterocycle compounds and preparation method thereof
  • Imidazo-[1,2-c]-quinazolin-3(2H)-one fused-heterocycle compounds and preparation method thereof
  • Imidazo-[1,2-c]-quinazolin-3(2H)-one fused-heterocycle compounds and preparation method thereof

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Experimental program
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preparation example Construction

[0048] The preparation method of the condensed ring compound of the present invention is: under the action of compound 1 (amine 1) and compound 2 (amine 2), react for 2 to 50 hours in an appropriate solvent and an appropriate temperature of 0 to 160 ° C to form a key intermediate Namely 3 in the following general formula. Feeding of the reactant and solvent: The molar ratio of compound 1: compound 2: solvent is 1:1-30:0-200. Intermediate compound 3 and compound 4 were reacted in a suitable solvent at 0-160°C for 2-48 hours, and after purification, condensed ring compound 5 represented by the following general formula was obtained.

[0049]

[0050] 1. Compound 1, compound 2 and the solvent are put into the reaction bottle according to a certain ratio.

[0051] 2. The reaction mixture is reacted at 0-160°C for 2-50 hours.

[0052] 3. The primary product intermediate compound 3 was isolated and used directly in the next step.

[0053] 4. Put compound 3, compound 4 and ...

Embodiment 1

[0056]

[0057] React first step:

[0058] Add 11.8 g (0.1 mol) of 2-aminobenzonitrile and 50 g of N,N-dimethylformamide dimethyl acetal into a 100 ml single-necked round bottom flask. A mixed solvent of tetrahydrofuran and acetonitrile was added, and the mixture was heated to reflux and stirred for 2 hours. TLC and HPLC analysis indicated the reaction was complete. Recovery of N,N-dimethylformamide dimethyl acetal. The residue was dried to obtain the pure intermediate (E)-N'-(2-carbonitrile benzene)-N,N-dimethylmethylimidium [(E)-N'-(2-cyanophenyl)-N,N- dimethylformimidamide]. 17.2 g of the product was obtained, with a yield of 99.4%. 1 h NMR (CDCl 3 ) 300MHz, ppm, 8.03 (1H, s), 7.59 (1H, m), 7.45 (1H, m), 7.0-7.16(2H, m), 2.95 (3H, s), 2.97 (3H, s); MS , m / z (M+1): 174.10.

[0059] React second step:

[0060] Add 1.73 g (0.01 mol) of (E)-N'-(2-carbonitrile benzene)-N,N-dimethylmethylamine and 3.06 g of ethyl glycine into a 10 ml single-necked round bottom flask...

Embodiment 2

[0062]

[0063] React first step:

[0064] 11.8 g (0.1 mol) of 2-aminobenzonitrile and 60 g of N,N-dimethylformamide dimethyl acetal were added to a 50 ml single-necked round bottom flask, and tetrahydrofuran was added as a solvent. The mixture was heated to reflux. TLC and HPLC analysis indicated the reaction was complete. Recovery of N,N-dimethylformamide dimethyl acetal. The pure intermediate (E)-N'-(2-cyanophenyl)-N,N-dimethylformimidamide [(E)-N'-(2-cyanophenyl)-N,N-dimethylformimidamide] was obtained. 17.3 g of the product was obtained, and the yield was 100%. 1 h NMR (CDCl 3 ) 300MHz, ppm, 8.03 (1H, s), 7.59 (1H, m), 7.45 (1H, m), 7.0-7.16(2H, m), 2.95 (3H, s), 2.97 (3H, s); MS , m / z (M+1): 174.10.

[0065] React second step:

[0066] Add 2.33 g (0.01 mol) of (E)-N'-(2-carbonitrile benzene)-N,N-dimethylmethylamide and 3.03 g of ethyl glycine into a 10 ml single-necked round bottom flask, and then add di Methyl sulfoxide 10 ml. The reaction mixture was sti...

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Abstract

The invention discloses imidazo-[1,2-c]-quinazolin-3(2H)-one fused-heterocycle compounds and a preparation method thereof, and discloses a preparation method of fused ring compounds (imidazo[1,2-c]quinazolin-3(2H)-one derivatives). The preparation method comprises the steps that 3 in a general formula is obtained by reacting at the proper temperature in the absence of a solvent or in a proper amount of the solvent under the action of amines 1 and 2 to generate a key intermediate and purifying; in addition, if R2 is -H, 3 can also be obtained by reacting 1 and DMF in the presence of benzene sulfonyl chloride and purifying, and the fused ring compounds represented by a formula are obtained by reacting 3 with 4 at the proper temperature in a proper amount of the solvent. The method has the beneficial effects that 1, the reaction path is short, namely a two-step synthetic method is adopted; 2, two heterocyclic rings are formed by adopting a one-pot method in the reaction of the second step; 3, raw materials are easily available and the operation is convenient; 4, no heavy metal ion catalysts and the like are used in the reaction and the reaction conditions are mild; 5, the reaction time is moderate, the control is easy, the post-treatment is simple, and the product purity and the yield are high; 6, the environment is not polluted and the green chemical concept is fully embodied.

Description

Technical field [0001] The present invention involves fine organic synthesis fields, and specifically involves a type of thick hybrid compounds and their preparation methods, especially a type of pyramole [1,2-C] -nezoline-3 (2H)-ketone thick ring compounds and their preparationmethod. Background technique [0002] The synthesis and application of thick metrological compounds have always been one of the hot spots of organic synthetic chemistry.It is used in insecticides, thick herbicides, antitumor, cardiovascular drugs, antibacterial drugs and chemotherapy materials, chemical light emitting materials, conductive polymer, new structured dyes and thick rings flavors.s concern.Herbotiated herbicides, especially thick circulation, will live in a dominant position. High toxic pesticides like organic phosphorus pesticides will gradually be eliminated, and they will be replaced by ultra -efficient thick -ring new insecticides.The thick ring is also an important application in the dye i...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/04
CPCC07D487/04
Inventor 刘雪静
Owner ASSET SUZHOU PHARMA CO LTD
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