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8, 9-mono and/or di-substituted imidazo[1, 2-c]quinazolin-3(2H)-one fused heterocyclic compound and preparation method thereof

A compound, 2-c technology, applied in the direction of organic chemistry, can solve problems such as low yield and limited application

Active Publication Date: 2014-09-24
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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  • 8, 9-mono and/or di-substituted imidazo[1, 2-c]quinazolin-3(2H)-one fused heterocyclic compound and preparation method thereof
  • 8, 9-mono and/or di-substituted imidazo[1, 2-c]quinazolin-3(2H)-one fused heterocyclic compound and preparation method thereof
  • 8, 9-mono and/or di-substituted imidazo[1, 2-c]quinazolin-3(2H)-one fused heterocyclic compound and preparation method thereof

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Experimental program
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preparation example Construction

[0054] The invention provides a preparation method of a class of fused ring compounds [8,9-mono and / or di-substitutedimidazo[1,2-c]quinazolin-3(2H)-one derivatives], comprising the following steps: Under the action of compound 2, the key intermediate is generated by reaction in the absence of solvent or in a suitable solvent and at a suitable temperature, and the intermediate 3 in the following general formula can be obtained after purification. If R 3 = -H, intermediate 3 can also be obtained by purification of amine 1 and DMF under the action of benzenesulfonyl chloride. Then intermediate 3 reacts with compound 4 in a suitable solvent and at a suitable temperature to obtain condensed ring compound 5 represented by the following general formula.

[0055] The preparation method of the condensed ring compound of the present invention is to react for 1-48 hours under the action of amine 1 and compound 2 in the absence of solvent or a suitable solvent and a suitable temperature...

Embodiment 1

[0079]

[0080] React first step:

[0081] Add 17.8 grams (0.1 moles) of 2-amino-4,5-dimethoxybenzonitrile, 20 grams of N,N-dimethylformamide dimethyl acetal and 10 mL of toluene, the reaction mixture was heated for 50 o C and hold for 3 hours. TLC and HPLC analysis indicated the reaction was complete. Separation and removal of excess N,N-dimethylformamide dimethyl acetal and solvent, the residue was washed, purified and dried to obtain pure intermediate (E)-N'-(2-carbonitrile-4,5 -Dimethoxyphenyl)-N,N-dimethylformimidamide [(E)-N'-(2-cyano-4,5 dimethoxy-phenyl)-N,N-dimethylformimidamide]. 21.9 g of the product was obtained, with a yield of 94.0%. 1 H NMR (CDCl 3 ) 300 MHz (ppm): 8.04 (1H, s), 7.73 (1H, s), 6.79(H, s), 3.80 (3H, s), 3.94 (3H, s), 2.95 (3H, s), 2.97 (3H, s); MS: m / z (M+1) 234.10.

[0082] React second step:

[0083] Add (E)-N'-(2-carbonitrile-4,5-dimethoxybenzene)-N,N-dimethylmethylamide 2.33 g (0.01 mol) into a 25 ml single-necked round bottom flask...

Embodiment approach 2

[0085]

[0086] React first step

[0087] Add 21.2 g (0.1 mol) of 2-amino-4,5-dimethoxybenzonitrile, 90 g of N,N-dimethylformamide dimethyl acetal and tetrahydrofuran into a 250 ml single-necked round bottom flask 100 ml, and the reaction mixture was heated to reflux. TLC and HPLC analysis indicated the reaction was complete. Separation and recovery of N,N-dimethylformamide dimethyl acetal. The residue was washed, purified, and dried to obtain the pure intermediate (E)-N'-(2-carbonitrile-4,5-dimethoxybenzene)-N,N-dimethylmethane [(E) -N'-(2-cyano-4,5 dimethoxy-phenyl)-N,N-dimethylformimidamide]. 25.5 g of the product was obtained, with a yield of 92%. 1 H NMR (CDCl 3 ) 300 MHz (ppm): 8.04 (1H, s), 7.73 (1H, s), 6.79(H, s), 3.80 (3H, s), 3.94 (3H, s), 2.95 (3H, s), 2.97 (3H, s); MS: m / z (M+1) 234.10.

[0088] React second step:

[0089] Add (E)-N'-(2-carbonitrile-4,5-dimethoxybenzene)-N,N-dimethylmethylamide 2.93 g (0.01 mol) into a 25 ml single-necked round bottom f...

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Abstract

The invention discloses a 8, 9-mono and / or di-substituted imidazo[1, 2-c]quinazolin-3(2H)-one fused heterocyclic compound and a preparation method thereof. The method comprises the steps of: reacting amine 1 and a compound 2 without solvent or in an appropriate solvent under an appropriate temperature to generate a key intermediate, then performing purification to obtain an intermediate 3 shown as the following general formula, or if R3=-H, reacting amine 1 and DMF under the action of benzenesulfonyl chloride and then conducting purification to obtain the intermediate 3, and then reacting the intermediate 3 with a compound 4 in an appropriate solvent under an appropriate temperature to obtain a fused ring compound 5 shown as the following general formula. The method provided by the invention has the advantages that: 1. the reaction route is short, i.e. a two-step synthesis method; 2. the fused ring compound with two heterocycles is formed in step 2 by a one-pot technique; 3. the raw materials are easily available, and the operation is convenient; 4. the reaction has no need for any heavy metal ion catalyst and the like, and the reaction conditions are mild; 5. the reaction time is moderate, the reaction is easy to control, the post-treatment is simple, and the product has high purity and yield; and 6. the method has no pollution to the environment, thus fully reflecting the concept of green chemistry.

Description

technical field [0001] The invention relates to the field of fine organic synthesis, in particular to the preparation of a class of imidazo[1,2-c]-quinazolin-3(2H)-one condensed heterocyclic compounds, specifically the invention discloses a class of condensed ring Compound 8, 9-Mono- and di-substituted imidazo[1,2-c]-quinazolin-3(2H)-one condensed heterocyclic compound [8,9-mono and / or di-substitutedimidazo[1,2- c] synthetic preparation method of quinazolin-3 (2H)-one derivative]. Background technique [0002] Fused heterocyclic compounds are increasingly used in insecticides, herbicides, antitumor and cardiovascular drugs, antibacterial drugs and chemotherapy, chemiluminescent materials, conductive polymers, dyes with new structures, and fused heterocyclic flavors. s concern. Fused heterocyclic herbicides will replace highly toxic organophosphorus pesticides and will be replaced by new ultra-efficient fused heterocyclic insecticides. Some heterocyclic condensed compounds...

Claims

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Application Information

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IPC IPC(8): C07D487/04
CPCC07D487/04
Inventor 刘雪静王峰
Owner ASSET SUZHOU PHARMA CO LTD
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