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: 2014-08-06
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

[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 solvent into the reaction flask at a molar ratio of 1:1-20:10-60, react at 0-160°C for 1-50 hours, and obtain the condensed ring compound represented by the following general formula after purification 5.

[0054] The invention discloses a class of condensed ring compounds [imidazo[1,2-c]quinazolin-3(2H)-one derivatives] and a preparation method thereof. Comprise the following steps: the preparation method of the condensed ring compound of the present invention is in amine 1 and 2 Under the action of no solvent or in a suitable solvent and at a suitable temperature, the reaction generates a key intermediate, which can be obtained ...

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 stir...

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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 invention relates to the field of fine organic synthesis, in particular to a class of fused heterocyclic compounds and a preparation method thereof, in particular to a class of imidazo[1,2-c]-quinazolin-3(2H)-one condensed ring compounds and their preparation method. Background technique [0002] The synthesis and application of fused heterocyclic compounds has always been one of the hot spots in organic synthetic chemistry. It is used more and more in pesticides, fused heterocyclic herbicides, anti-tumor, cardiovascular drugs, antibacterial drugs and chemotherapy, chemiluminescent materials, conductive polymers, dyes with new structures and fused heterocyclic flavors s concern. Heterocyclic compounds, especially fused heterocyclic herbicides will be dominant, and highly toxic insecticides such as organophosphorus pesticides will be phased out and replaced by ultra-efficient fused heterocyclic herbicides. Fused heterocycles also have important a...

Claims

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Application Information

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