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Substituted 1H pyrazolo [3,4-d] pyrimidin-4(5H)-ketone derivatives with weeding activity and preparation thereof

A 4-d, pyrazolo technology, applied in the field of multi-substituted 1H pyrazolo [3, can solve the problems of many steps, long reaction time, harsh conditions, etc.

Inactive Publication Date: 2010-07-14
HUAZHONG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] At present, there are relatively few reports on the synthesis of pyrazolo[3,4-d]pyrimidine compounds. There are two main routes to synthesize such compounds. One is to synthesize the corresponding pyrimidine ring from the pyrazole ring by ring closure , the second is to start from the pyrimidine ring and synthesize the pyrazole ring through corresponding ring closure to obtain pyridopyrimidine compounds. The existing methods require relatively harsh conditions, long reaction time and many steps
[0007] There are few reports on the biological activity of pyrazolo[3,4-d]pyrimidine compounds

Method used

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  • Substituted 1H pyrazolo [3,4-d] pyrimidin-4(5H)-ketone derivatives with weeding activity and preparation thereof
  • Substituted 1H pyrazolo [3,4-d] pyrimidin-4(5H)-ketone derivatives with weeding activity and preparation thereof
  • Substituted 1H pyrazolo [3,4-d] pyrimidin-4(5H)-ketone derivatives with weeding activity and preparation thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Preparation of Compound 1

[0040]

[0041] In a dry round bottom flask, add 1mmol of phosphinimine, then add 15mL of anhydrous dichloroethane to dissolve, add 1.1mmol of p-chlorophenyl isocyanate dropwise, and after standing for 6 hours below 10°C, add 1.1mmol of Ethylamine, stirred and reacted for 1 hour, after the reaction was complete, removed most of the solvent under reduced pressure, then added 15mL of absolute ethanol and 0.6mmol triethylamine solution, stirred and reacted for 12 hours below 0°C, and precipitated out, After filtration and recrystallization with dichloroethane / petroleum ether, the pure product of the target compound was obtained as a white solid with a yield of 76.7%. M.p.162.8~163.9℃;

[0042] Elemental analysis (%): Calculated value (C 22 h 22 ClN 5 OS): C, 60.06; H, 5.04; N, 15.92; S, 7.29; Found: C, 59.79; H, 4.69; N, 15.36; S, 7.05;

[0043] 1 H NMR (CDCl 3 , 400MHz) δ (ppm): 0.92 (t, J = 6.8, 6H, 2CH 3 ), 2.65(s, 3H, SCH 3 ), 3....

Embodiment 2

[0072] Preparation of compound 3

[0073]

[0074] In a dry round bottom flask, add 1mmol of phosphinimine, then add 15mL of anhydrous chloroform to dissolve, add 1.2mmol of p-chlorophenyl isocyanate dropwise, react at below 50°C for 24 hours, then add 1.2mmol of diisopropylamine , stirred and reacted for 24 hours, after the reaction was complete, removed most of the solvent under reduced pressure, then added 15mL of anhydrous isopropanol and 1.0mmol pyridine solution, stirred and reacted for 8 hours below 20°C, precipitated, filtered, Recrystallized with chloroform / petroleum ether, the pure product of the target compound was obtained as white crystals, with a yield of 79.6%, m.p.158.1-159.6°C;

[0075] 1 H NMR (CDCl 3 , 400MHz) δ (ppm): 1.12 (d, J = 6.8, 12H, 4CH 3 ), 1.37~1.40 (m, 4H, 2CH 2 ), 2.65(s, 3H, SCH 3 ), 3.58~3.60(m, 2H, 2CH), 7.15~8.05(m, 9H, Ph-H);

[0076] IR(KBr)υ(cm-1 ):: 3065(Ph-H), 1701(C=O), 1596, 1431(Ph), 1534(C=N), 1256(C-N);

[0077] Elemental...

Embodiment 3

[0104] Preparation of compound 5

[0105]

[0106] In a dry round-bottomed flask, add 1 mmol of phosphinimine, then add 15 mL of anhydrous ether to dissolve, add 0.9 mmol of p-chlorophenyl isocyanate dropwise, and let it stand for reaction below -20°C for 12 hours, then add 1.0 mmol of di-n- Pentylamine, stirred and reacted for 24 hours, after the reaction was complete, removed most of the solvent under reduced pressure, then added 15mL of anhydrous n-propanol and 0.9mmol diethylamine solution, stirred and reacted for 6 hours below 0°C, and there was precipitation Precipitate, filter, and recrystallize with dichloromethane / petroleum ether to obtain the pure product of the target compound as white crystals, with a yield of 77.3%, m.p.119.3-121.2°C;

[0107] 1 H NMR (CDCl 3 , 400MHz) δ (ppm): 0.86 (t, J = 7.2, 6H, 2CH 3 ), 1.08~1.12 (m, 4H, 2CH 2 ), 1.14~1.35(m, 8H, 4CH 2 ), 2.66(s, 3H, SCH 3 ), 3.05(t, J=7.6, 4H, 2CH 2 ), 7.24~8.16(m, 9H, Ph-H);

[0108] IR(KBr)υ(cm ...

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Abstract

The invention discloses substituted 1H pyrazolo [3,4-d] pyrimidin-4(5H)-ketone derivatives with weeding activity, which have a general formula I, and preparation thereof. In the formula, R1 is methyl, benzyl or substituted benzyl; a substituting group on phenyl of the benzyl is halogen or nitryl and mono-substitution or multi-substitution at any position of a benzene ring is the same or different; X is S or SO2; Ar is phenyl or substituted phenyl; a substituting group on the phenyl is halogen or nitryl and mono-substitution or multi-substitution at any position of a benzene ring is the same or different; R2 is phenyl or substituted phenyl; a substituting group on the phenyl is halogen and mono-substitution or multi-substitution at any position of a benzene ring is the same or different; R3 is C1-C8 mono-alkyl amido, C1-C6 dialkyl amido, benzene alkyl (C1-C4) amido or substituted benzene alkyl (C1-C4) amido, piperidyl or morpholine group; and a substituting group on the phenyl related to the R3 is halogen, C1-C6 alkyl or alkoxy, and the mono-substitution or multi-substitution at any position of a benzene ring is the same or different. The compounds can be used as active ingredients of a herbicide.

Description

technical field [0001] The present invention relates to the preparation method of multi-substituted 1H pyrazolo[3,4-d]pyrimidin-4(5H)-one compound with herbicidal activity and its intermediate, as well as its biological activity as a potential herbicide. Background technique [0002] Pyrazolopyrimidine compounds have a wide range of biological activities, and have antibacterial, anti-inflammatory, gout, and antiviral effects in medicine. There are also reports in the literature that they have good activity on cytotoxins and can selectively inhibit phosphate diphosphate Esterase may be developed into cardiotonic drugs, antidepressants, etc. In addition, there are some reports on the activity on pesticides. [0003] According to their structural characteristics, there are three main types of pyrazolopyrimidine compounds: pyrazolo[1,5-a]pyrimidine, pyrazolo[3,4-d]pyrimidine and pyrazolo[4,3-d] pyrimidine. Its general formula is as follows: [0004] [0005] Pyrazolo[1,5-...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04A01N43/90A01P13/00
Inventor 贺红武任青云粱英
Owner HUAZHONG NORMAL UNIV