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Novel synthesis method of 9,5-substituted imidazole [1, 2-c]-quinazoline-3(2H)-ketone thick heterocyclic compound

A synthetic method, 2-c technology, applied in the direction of organic chemistry, etc., can solve the problems of high yield, low toxicity, and few steps, and achieve the effect of high reaction yield, mild reaction conditions, and simple process

Inactive Publication Date: 2014-12-10
刘雪静
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  • Claims
  • Application Information

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Problems solved by technology

The method has few steps, high yield, low toxicity (does not contain reagents such as phosphorus) and is easy to operate, which overcomes the deficiencies in the existing synthesis methods of such fused heterocyclic compounds

Method used

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  • Novel synthesis method of 9,5-substituted imidazole [1, 2-c]-quinazoline-3(2H)-ketone thick heterocyclic compound
  • Novel synthesis method of 9,5-substituted imidazole [1, 2-c]-quinazoline-3(2H)-ketone thick heterocyclic compound
  • Novel synthesis method of 9,5-substituted imidazole [1, 2-c]-quinazoline-3(2H)-ketone thick heterocyclic compound

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] The first step of the reaction: add 16.3 grams of 2-amino-5-nitrobenzonitrile and 12.1 grams of N,N-dimethylformamide dimethyl acetal to a 50 ml single-necked round bottom flask, add 25 ml of toluene , the reaction mixture was stirred at 50°C for 4 hours; TLC analysis showed that after the reaction was complete, N,N-dimethylformamide dimethyl acetal and solvent were removed by rotary evaporation, and the residue was washed with cold ether and then dried in vacuo 21.7 g of pure light yellow intermediate (E)-N'-(2-carbonitrile-4-nitrophenyl)-N,N-dimethylmethylamide was obtained with a yield of 95%.

[0028] Its structure and characterization data are as follows:

[0029] 1 H NMR (DMSO d6 ) 300 MHz (ppm): 8.42 (1H, s), 8.37 (1H, m), 8.01 (H, s), 7.56 (1H, m), 2.96 (3H, s), 2.99 (3H, s); MS : m / z (M+1) 219.01.

[0030] The second step of the reaction: add (E)-N'-(2-carbonitrile-4-nitrophenyl)-N,N-dimethylmethylamide 2.18 g and glycine B in a 25 ml single-necked round bo...

Embodiment 2

[0036] The first step of the reaction: add 21.5 grams of 2-amino-5-nitrobenzonitrile and 15.7 grams of N,N-dimethylformamide dimethyl acetal to a 50 ml single-necked round bottom flask, and add tetrahydrofuran as a solvent , the reaction mixture was stirred at 15°C for 2 hours; TLC analysis showed that the reaction was complete, N,N-dimethylformamide dimethyl acetal and solvent were separated and recovered, the residue was extracted with dichloromethane, washed with water, anhydrous sodium sulfate Drying, filtration, and rotary evaporation yielded 28.2 g of pure light yellow intermediate (E)-N'-(2-carbonitrile-4-nitrophenyl)-N,N-dimethylmethylamide, yield 98 %.

[0037] Its characterization data are as follows:

[0038] 1 H NMR (DMSO d6 ) 300 MHz (ppm): 8.42 (1H, s), 8.37 (1H, m), 8.01 (H, s), 7.56 (1H, m), 2.96 (3H, s), 2.99 (3H, s); MS : m / z (M+1) 219.01.

[0039] The second step of the reaction: add 4.8 grams of (E)-N'-(2-formonitrile-4-nitrophenyl)-N,N-dimethylmethyla...

Embodiment 3

[0044] The first step of the reaction: add 36.8 grams (0.1 mole) of 2-amino-5-nitrobenzonitrile and 25.6 grams of N,N-dimethylformamide dimethyl acetal to a 50 ml single-necked round bottom flask, Toluene was added as a solvent, and the reaction mixture was stirred at 80°C for 1 hour; TLC analysis showed that the reaction was complete; N,N-dimethylformamide dimethyl acetal and solvent were separated and recovered, and the residue was extracted with dichloromethane, washed with water, and free Dry over sodium sulfate, filter, and rotary evaporate to obtain 48.7 g of pure light yellow intermediate (E)-N'-(2-carbonitrile-4-nitrophenyl)-N,N-dimethylmethane, Yield 99%.

[0045] Its characterization data are as follows:

[0046] 1 H NMR (DMSO d6 ) 300 MHz (ppm): 8.42 (1H, s), 8.37 (1H, m), 8.01 (H, s), 7.56 (1H, m), 2.96 (3H, s), 2.99 (3H, s); MS : m / z (M+1) 219.01.

[0047] The second step of the reaction: add (E)-N'-(2-carbonitrile-4-nitrophenyl)-N,N-dimethylmethylamide 5.6 g...

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Abstract

The invention discloses a novel synthesis method of a 9,5-substituted imidazole [1, 2-c]-quinazoline-3(2H)-ketone thick heterocyclic compound. The novel synthesis method of the 9,5-substituted imidazole [1, 2-c]-quinazoline-3(2H)-ketone thick heterocyclic compound comprises the following steps: step one, reacting amine (1) with a compound (2) at 0-180 DEG C for 1-48 hours in the absence of a solvent or in the presence of a proper solvent, carrying out rotary evaporation to remove the excess reactants and solvent, purifying and drying residue to obtain a key compound intermediate (3); and step two, reacting the intermediate (3) with alpha amino acid ester at 0-160 DEG C in the proper solvent for 1-48 hours, carrying out rotary evaporation to remove the solvent, purifying residue to obtain a target product which is a thick heterocyclic compound (5). The novel synthesis method of the 9,5-substituted imidazole [1, 2-c]-quinazoline-3(2H)-ketone thick heterocyclic compound is short in reaction route, mild in reaction conditions, moderate in reaction time and easy to control, adopts easily available raw materials, can produce a high-purity product with high yield, and does not pollute the environment.

Description

technical field [0001] The present invention relates to a synthesis method of quinazolinone condensed heterocyclic compounds, in particular to a novel 9,5-substituted imidazo[1,2-c]-quinazolin-3(2H)-one condensed heterocyclic ring The invention relates to a compound synthesis method, which belongs to the fields of fine chemical industry and drug synthesis research. Background technique [0002] The application of fused heterocyclic compounds in insecticides, herbicides, antitumor and antibacterial drugs and chemotherapy, chemiluminescent materials, conductive polymers, dyes with new structures, and fused heterocyclic fragrances has attracted more and more attention. Among them, typical fused heterocyclic compounds are quinazolinone compounds and their derivatives. [0003] Quinazolinone compounds are the main structural units of many alkaloids. Studies in recent years have shown that quinazolinone compounds have multiple biological activities and a wide range of pharmacolog...

Claims

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Application Information

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IPC IPC(8): C07D487/04
CPCC07D487/04
Inventor 刘雪静孔军吴鸿伟
Owner 刘雪静
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