2H-imidazo[1,2-C] quinazoline-3-one compound with optical activity and preparation method thereof

A technology of optically active and ketone compounds, applied in the direction of organic chemistry, can solve the problems of limited application and low yield, and achieve the effects of convenient operation, easy availability of raw materials, high product purity and yield

Inactive Publication Date: 2015-02-04
SHANDONG ENG & TECH INST OF LUNAN COAL CHEM ENG
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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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  • 2H-imidazo[1,2-C] quinazoline-3-one compound with optical activity and preparation method thereof
  • 2H-imidazo[1,2-C] quinazoline-3-one compound with optical activity and preparation method thereof
  • 2H-imidazo[1,2-C] quinazoline-3-one compound with optical activity and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026]

[0027] React first step

[0028] Add 11.8 g (0.10 mol) of 2-aminobenzonitrile and 50 g of N,N-dimethylformamide dimethyl acetal into a 100 ml single-necked round bottom flask. 20 ml of toluene was added, and the reaction mixture was stirred at room temperature for 4 hours. TLC and HPLC analysis indicated the reaction was complete. Rotary evaporation recovers N,N-dimethylformamide dimethyl acetal and solvent. The residue was vacuum-dried to obtain the pure intermediate (E)-N'-(2-cyanophenyl)-N,N-dimethylmethylimidium [(E)-N'-(2-cyanophenyl)-N, N-dimethylformimidamide] 17.2 grams, yield 99.4%. 1 H NMR (CDCl 3 ) 300 MHz, ppm: 8.03 (1H, s), 7.55 (1H, m), 7.45 (1H, m), 7.10-7.20 (2H, m), 2.95 (3H, s), 2.97 (3H, s); MS: m / z (M+1) 174.09.

[0029] React second step

[0030] Add 1.73 g (0.010 mol) of (E)-N'-(2-carbonitrile benzene)-N,N-dimethylmethylamine and 1.8 g of ethyl aminophenylacetate into a 50 ml single-necked round bottom flask, Then 10 ml each of acetic ...

Embodiment 2

[0032]

[0033] React first step

[0034] 8.8 g (0.074 mol) of 2-aminobenzonitrile and 47 g of N,N-dimethylformamide dimethyl acetal were added to a 100 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. Recover N,N-dimethylformamide dimethyl acetal and solvent. The pure intermediate (E)-N'-(2-cyanophenyl)-N,N-dimethylformimidamide [(E)-N'-(2-cyanophenyl)-N,N-dimethylformimidamide] 12.5 grams, yield 96.9%. 1 H NMR (CDCl 3 ) 300 MHz, ppm: 8.03 (1H, s), 7.55 (1H, m), 7.45 (1H, m), 7.10-7.20 (2H, m), 2.95 (3H, s), 2.97 (3H, s); MS: m / z (M+1) 174.09.

[0035] React second step

[0036] Add 1.89 g (0.011 mol) of (E)-N'-(2-carbonitrile benzene)-N,N-dimethylmethylamine and 3.9 g of ethyl aminophenylacetate into a 50 ml single-necked round bottom flask, Then 10 ml each of acetic acid and dimethyl sulfoxide was added. The reaction mixture was heated...

Embodiment 3

[0038]

[0039] React first step

[0040] 16.8 g (0.142 mol) of 2-aminobenzonitrile and 40 g of N,N-dimethylformamide dimethyl acetal were added to a 100 ml single-necked round bottom flask, and xylene was added as a solvent. The mixture was heated to reflux. TLC and HPLC analysis indicated the reaction was complete. Recover N,N-dimethylformamide dimethyl acetal and solvent. The pure intermediate (E)-N'-(2-cyanophenyl)-N,N-dimethylformimidamide [(E)-N'-(2-cyanophenyl)-N,N-dimethylformimidamide] 24.2 grams, yield 98.2%. 1 H NMR (CDCl 3 ) 300 MHz, ppm: 8.03 (1H, s), 7.55 (1H, m), 7.45 (1H, m), 7.10-7.20 (2H, m), 2.95 (3H, s), 2.97 (3H, s); MS: m / z (M+1) 174.09.

[0041] React second step

[0042] Add 4.33 g (0.025 mol) of (E)-N'-(2-carbonitrile benzene)-N,N-dimethylmethylamide and 4.9 g of ethyl aminophenylacetate into a 50 ml single-necked round bottom flask, Then 10 mL each of acetic acid and butanol was added. The reaction mixture was heated and stirred at 100...

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Abstract

The invention discloses a 2H-imidazo[1,2-C] quinazoline-3-one compound with optical activity and a preparation method thereof. The preparation method comprises the steps of reacting to generate a key intermediate shown in the formula in the specification at appropriate temperature in the absence of solvent or in an appropriate solvent under the actions of amine 1 and a compound 2, wherein when R2 is -H, the intermediate 3 can be generated by the amine 1 and DMF under the action of benzene sulfonyl chloride, and the intermediate 3 can be obtained through separation and purification; and reacting the intermediate 3 with alpha amino-acid ester 4 or 4' at appropriate temperature in an appropriate solvent, and purifying to obtain quinazolinone compounds 5 and 6 shown in the formula in the specification. The reaction route is short, the two-step synthesis method is adopted, the raw materials are easily available, the operation is convenient, no any heavy metal ionic catalyst and the like are added during reaction, the product has high purity and high yield, no environment pollution is caused, and the green chemistry concept is fully embodied.

Description

technical field [0001] The invention relates to the field of fine organic synthesis, in particular to an optically active 2H-imidazo[1,2-C]quinazolin-3-one compound and a preparation method thereof. Background technique [0002] (R)-2H-imidazo[1,2-C]quinazolin-3-one and (S)-2H-imidazo[1,2-C]quinazolin-3-one derivatives are a class of derivatives with good Biologically active quinazolinone compounds have excellent activities in anti-tumor, anti-inflammation, anti-hypertensive and antibacterial drugs, so they are usually designed and constructed on the structure of certain molecules, thus endowing these molecules with new medical functions . It has always been a hot spot in medicinal chemistry research. In addition, quinazolinone compounds are also used in electroluminescence, solar energy conversion, liquid crystal materials, laser materials and other fields. Therefore, the synthesis and application of quinazolinones have always been one of the hot spots in organic synthet...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04
CPCC07D487/04
Inventor 刘雪静孔军吴鸿伟黄薇
Owner SHANDONG ENG & TECH INST OF LUNAN COAL CHEM ENG
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