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Substitution thieno[3',2':5,6]-pyridino[4,3-d]-pyrimidine-4(3H)-ketone and preparation method

A technology of thiophene and pyridine, which is applied in the field of substituted thieno[3',2':5,6]pyrido[4,3-d]pyrimidin-4(3H)-one with bactericidal activity and its preparation. Solve the problems of few reports on pesticide activity, many steps and harsh conditions

Inactive Publication Date: 2007-05-30
HUAZHONG NORMAL UNIV
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  • Abstract
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AI Technical Summary

Problems solved by technology

[0007] At present, there are relatively few reports on the synthesis of pyrido[4,3-d]pyrimidine compounds. There are two main routes to synthesize such compounds. The second is to start from the pyrimidine ring and synthesize the pyridine ring through corresponding ring closure to obtain pyridopyrimidine compounds. These methods require relatively harsh conditions, long reaction time and many steps.
[0008] The biological activity of pyrido[4,3-d]pyrimidine compounds is mainly limited to the pharmacological activity, and there are few reports on its pesticide activity.

Method used

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  • Substitution thieno[3',2':5,6]-pyridino[4,3-d]-pyrimidine-4(3H)-ketone and preparation method
  • Substitution thieno[3',2':5,6]-pyridino[4,3-d]-pyrimidine-4(3H)-ketone and preparation method
  • Substitution thieno[3',2':5,6]-pyridino[4,3-d]-pyrimidine-4(3H)-ketone and preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Preparation of Compound 1

[0040] In a dry round-bottomed flask, add 1 mmol of phosphinimine, then add 15 mL of anhydrous dichloroethane to dissolve, add 1.1 mmol of phenyl isocyanate dropwise, let it stand below 10°C for 6 hours, then add 1.1 mmol of n-propylamine, Stir the reaction for 1 hour. After the reaction is complete, remove most of the solvent under reduced pressure, then add 15 mL of absolute ethanol and 0.6 mmol sodium alkoxide solution, and stir the reaction for 12 hours below 15 ° C. There is precipitation, filter, and use two Chloroethane / petroleum ether was recrystallized to obtain the pure product of the target compound as a light yellow solid with a yield of 65%. M.p.243.1~243.6;

[0041] Elemental Analysis / %: Calculated: C, 68.87; H, 6.26; N, 13.39. Found: C, 69.14; H, 6.82; N, 13.57;

[0042] IR(υ / cm -1 ): 3445, 1677 (C=O), 1558, 1510, 1401, 1146, 806 cm -1 ;

[0043] 1 H NMR (δ / ppm): 7.25~7.65(m, 5H, Ar-H), 4.34(s, 1H, NH), 3.46(q, J=7.2Hz,...

Embodiment 2

[0073] Preparation of compound 3

[0074] In a dry round bottom flask, add 1mmol of phosphinimine, then add 15mL of anhydrous chloroform to dissolve, add 1.2mmol of phenyl isocyanate dropwise, react at below 50°C for 24 hours, then add 1.2mmol of isobutylamine, stir React for 24 hours. After the reaction is complete, remove most of the solvent under reduced pressure, then add 15mL of anhydrous n-propanol and 1.0mmol pyridine solution, and stir for 8 hours below 20°C. Precipitation occurs, filter, and use three Chloromethane / petroleum ether recrystallization, the pure product of the target compound was obtained as white crystals, the yield was 84%, m.p.232-233°C;

[0075] Elemental Analysis / %: Calculated: C 67.32, H 6.16, N 14.27; Found: C 67.01, H 5.71, N 13.92;

[0076] IR(υ / cm -1 ): 3375, 2951 (C-H), 2922 (C-H), 2866 (C-H), 1667 (C=O), 1558, 1518, 1449, 1384, 1297, 1267, 1174, 815, 770.;

[0077] 1 H NMR (δ / ppm): 0.86 (d, 3H, CH 3 ), 0.88 (d, 3H, CH 3 ), 1.95(m, 1H, ...

Embodiment 3

[0108] Preparation of compound 10

[0109] In a dry round bottom flask, add 1mmol of phosphinimine, then add 15mL of anhydrous ether to dissolve, add 0.9mmol of phenylisocyanate dropwise, let it stand for reaction below -20°C for 12 hours, then add 1.0mmol of diethylamine, Stir the reaction for 24 hours. After the reaction is complete, remove most of the solvent under reduced pressure, then add 15mL of anhydrous n-propanol and 0.9mmol diethylamine solution, and stir for 6 hours below 0°C. Precipitation occurs and is filtered. , recrystallized with dichloromethane / petroleum ether, the pure product of the target compound was obtained as white crystals, the yield was 80%, m.p.176-177°C;

[0110] Elemental Analysis / %: Calculated: C 67.32, H 6.16, N 14.27; Found: C 66.58, H 6.11, N 13.85;

[0111] IR(KBr, υ / cm -1 ): 3434, 2965 (C-H), 2926 (C-H), 1680 (C=O), 1550, 1515, 1491, 1416, 1380, 1351, 1312, 1284, 1252, 1185, 1064, 1045, 873, 694;

[0112] 1 H NMR (δ / ppm, CDCl 3 , TMS...

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Abstract

A substituent thieno [3', 2':5,6] pyrido [4,3-d] pyrimidine-4(3H)-one with bactericiding activity and its preparing process is also disclosed. It can be used as the bactericide with high suppression activity to cotton wilt fungus, the sheath and culm blight bacteria of rice, gray mold of cucumber, etc.

Description

[0001] Substituted thieno[3',2':5,6]pyrido[4,3-d]pyrimidin-4(3H)-one and its preparation technical field [0002] The present invention relates to the preparation method of polysubstituted thieno[3',2':5,6]pyrido[4,3-d]pyrimidin-4(3H)-one compound and its intermediate with fungicidal activity, and its Biological activity as a fungicide. Background technique [0003] Pyridopyrimidine compounds have become one of the research hotspots in the chemical field because of their remarkable biological activity. Pharmacological studies have shown that these compounds can be used for sterilization, anti-fungal, anti-tumor and cancer, anti-inflammatory, anti-gout, anti-stimulant, anti-allergic, anti-cardiovascular disease, anti-bronchitis, insecticide, plant conditioning, anti-inflammatory Folic acid, antihistamines, antivirals and phosphodiesterase inhibitors have good chemotherapeutic effects. Some of these compounds have also been developed into commercial products, such as sedativ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D495/16A01N43/90
Inventor 贺红武丁明武刘建超任青云崔泽平陈荷连
Owner HUAZHONG NORMAL UNIV
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