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Substitute 2,3-dihydrogen thiazole [4,5-d] pyrimidine-7(6H)- ketone (imines) having weed removal active and preparation thereof

The technology of dihydrothiazole and pyrimidine is applied in the field of substituted 2,3-dihydrothiazolo[4,5-d]pyrimidin-7(6H)-one (imine) with herbicidal activity and its preparation. Solve problems such as many steps, few reports on pesticide activity, and harsh conditions

Inactive Publication Date: 2007-09-26
HUAZHONG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] At present, there are relatively few reports on the synthesis of thiazolo[4,5-d]pyrimidine compounds. There are two main routes to synthesize such compounds. One is to synthesize the corresponding pyrimidine ring from the thiazole ring through ring-closing reaction, The second is to start from the pyrimidine ring and synthesize the thiazole ring through corresponding ring closure to obtain pyridopyrimidine compounds. The conditions required by these methods are relatively harsh, the reaction time is long, and there are many steps.
[0009] The biological activity of thiazolo[4,5-d]pyrimidines is mainly limited to pharmacological activity, and there are few reports on its pesticide activity.

Method used

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  • Substitute 2,3-dihydrogen thiazole [4,5-d] pyrimidine-7(6H)- ketone (imines) having weed removal active and preparation thereof
  • Substitute 2,3-dihydrogen thiazole [4,5-d] pyrimidine-7(6H)- ketone (imines) having weed removal active and preparation thereof
  • Substitute 2,3-dihydrogen thiazole [4,5-d] pyrimidine-7(6H)- ketone (imines) having weed removal active and preparation thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Preparation of Compound 1, Method A,

[0036] 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, and after standing at 10°C for 6 hours, add 1.1 One millimole of n-diethylamine, stirred and reacted for 1 hour, after the reaction was complete, removed most of the solvent under reduced pressure, then added 15 milliliters of absolute ethanol and 0.6 mmol of sodium alkoxide solution, and stirred and reacted for 12 hours at a temperature below 15°C. Precipitation was precipitated, filtered, and recrystallized with dichloroethane / petroleum ether to obtain the pure product of the target compound as a light yellow solid with a yield of 73.6%. M.p.206.2~207.1℃;

[0037] Elemental analysis (%): Calculated value (C 21 h 20 N 4 OS 2 ):: C, 61.74; H, 4.93; N, 13.71; S, 15.70; Found: C, 61.31; H, 5.01; N, 13.50; S, 15.23;

[0038] IR(υ / cm -1 ): 2974 (C-H), 1687 (C=O),...

Embodiment 2

[0066] Preparation of compound 3

[0067] In a dry round-bottomed flask, add 1 mmol of phosphinimine, then add 15 ml of anhydrous chloroform to dissolve, add 1.2 mmol of phenyl isocyanate dropwise, react at below 50°C for 24 hours, then add 1.2 mmol of Diisopropylamine, stirred and reacted for 24 hours. After the reaction was complete, removed most of the solvent under reduced pressure, then added 15 ml of anhydrous isopropanol and 1.0 mmol of pyridine solution, and stirred and reacted for 8 hours below 20°C. Precipitated, filtered, and recrystallized with chloroform / petroleum ether to obtain the pure product of the target compound as light yellow crystals, with a yield of 77.8%, m.p.254.1-255.6°C;

[0068] 1 H NMR (400MHz CDCl 3 ): δ (ppm): 0.82 (d, J=6.4, 12H, 4CH 3 ), 3.49 (m, 2H, 2CH), 7.25-7.58 (m, 10H, Ph-H);

[0069] IR(KBr)υ(cm -1 ): 2962 (C-H), 1689 (C=O), 1571, 1525 (Ph);

[0070] Elemental analysis (%). Calculated value (C 23 h 24 N 4 OS 2 :): C, 63.27; ...

Embodiment 3

[0103] Preparation of Compound 11

[0104] 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-chlorophenylisocyanate dropwise, and let it stand for reaction below -20°C for 12 hours, then add 1.0 mmol of diisopropylamine, stirred for 24 hours, after the reaction was complete, removed most of the solvent under reduced pressure, then added 15 ml of anhydrous n-propanol and 0.9 mmol of diethylamine solution, stirred below 0°C After reacting for 6 hours, a precipitate was precipitated, filtered, and recrystallized with dichloromethane / petroleum ether to obtain the pure product of the target compound as white crystals, with a yield of 79.7%, m.p.>270°C.

[0105] 1 H NMR (400MHz CDCl 3 ): δ (ppm): 0.85 (d, J=6.4, 12H, 4CH 3 ), 3.47(m, 2H, 2CH), 7.22-7.60(m, 9H, Ph-H);

[0106] IR(KBr)υ(cm -1 ): 2981 (C-H), 1675 (C=O), 1570, 1529 (Ph);

[0107] Elemental analysis (%). Calculated value (C 23 h 23 ClN ...

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Abstract

The invention discloses a multi-substituted-2, 3-dihydro-thiazole-[4, 5-d] pyrimidine-7(6H)-ketone (imine), wherein Y is O and NH; R1 is phenyl or substituted phenyl, which is halogen on the phenyl with substituted group at random position of phenyl ring to do the same or different single substitution or multiple substitutions; R2 is H, C1-C6 monoalkyl amino, C1-C6 dialkyl amino, phenyl amine, phenyl alkyl (C1-C4) amino or substituted pridefine (C1-C4) amino, heterocyclic substituted C1-C4 alkyl amino of furan, piperidine and morphia; R3 is C1-C8 alkyl, phenyl or substituted phenyl, pridefine (C1-C4) or substituted pridefine (C1-C4); the substituted group on the phenyl of R2 and R3 is halogen, C1-C6 alkyl or alkoxy, which can be the same or different.

Description

technical field [0001] The present invention relates to the preparation method of multi-substituted 2,3-dihydrothiazolo[4,5-d]pyrimidin-7(6H)-one (imine) compound and its intermediate with herbicidal activity, and its use as herbicide biological activity. Background technique [0002] Thiazolopyrimidine is an important analogue of purine, and its remarkable biological activity is attracting more and more attention. Pharmacological studies have confirmed that 7-thia-8-oxoguanosine (7-thia-8-oxoguanosine) has an inhibitory effect on various viral infections in organisms, and has entered the clinical trial stage as an immunotherapy drug for viral infections; Lewis et al. Studies have proved that these compounds have a good inhibitory effect on human HCMV virus. In addition, a large number of studies have shown that these compounds have good chemotherapeutic effects in terms of sterilization, anti-tumor, sedation, and rheumatism. In plant protection, the microbicidal and inse...

Claims

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Application Information

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IPC IPC(8): C07D513/04A01N43/90A01P13/00
Inventor 贺红武梁英
Owner HUAZHONG NORMAL UNIV
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