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Tetralin pyrazolone triazine compound as well as preparation method and application thereof

A technology of triazine compound and tetrahydropyrazolone, which is applied in the field of organic compound preparation, can solve the problems of high cost and complicated preparation method, and achieve the effects of low cost, simple preparation method and high yield

Active Publication Date: 2015-09-09
HENAN AGRICULTURAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The above preparation method is limited by the raw materials of ylides, and needs to use transition metals and expensive catalysts. The preparation method is complicated and the cost is high.

Method used

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  • Tetralin pyrazolone triazine compound as well as preparation method and application thereof
  • Tetralin pyrazolone triazine compound as well as preparation method and application thereof
  • Tetralin pyrazolone triazine compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025]

[0026] Add 2-(phenyl)pyrazolidine 3-ketoylide (0.125mmol), N-methoxy-N-trimethylsilylbenzylamine (Ⅲ) (0.125mmol) into a 15mL reaction tube, then add CH 2 Cl 2 (1 mL) and trifluoroacetic acid (0.0125 mmol). Then N-methoxy-N-trimethylsilylbenzylamine (Ⅲ) (0.375 mmol) was added in batches, and the reaction system was stirred at 10° C. for 72 h until the reaction was complete. The reaction solution was spin-dried and directly purified by silica gel column chromatography (eluent: petroleum ether / ethyl acetate=1 / 9) to obtain a white solid. 71% yield, a white solid. 1 H NMR (400MHz, Chloroform-d) δ7.36–7.27(m,10H),4.91(d,J=11.3Hz,1H),3.78–3.68(m,4H),3.36–3.25(m,1H), 2.96–2.89(m,1H),2.84–2.75(m,1H),2.69–2.60(m,2H),2.50–2.39(m,1H); 13 C NMR (101MHz, CDCl 3 )δ170.35, 138.03, 137.03, 129.04, 128.75, 128.52, 128.33, 127.74, 127.52, 66.99, 61.58, 58.68, 57.61, 47.96, 30.09; IR (film) ν max 3029,2924,2844,1695,1602,1494,1453,1410,1328,1280,1129,1065,1027,929,979,758,100,6...

Embodiment 2

[0028]

[0029] Add 2-(o-methylphenyl)pyrazolidine 3-ketoylide (0.125mmol) and N-methoxy-N-trimethylsilylbenzylamine (Ⅲ) (0.125mmol) into a 15mL reaction tube, Then add CH 2 Cl 2 (1 mL) and trifluoroacetic acid (0.0125 mmol). Then N-methoxy-N-trimethylsilylbenzylamine (Ⅲ) (0.375 mmol) was added in batches, and the reaction system was stirred at 10° C. for 72 h until the reaction was complete. The reaction solution was spin-dried and directly purified by silica gel column chromatography (eluent: petroleum ether / ethyl acetate=1 / 9) to obtain a white solid. 69% yield, a white solid. 1 H NMR (400MHz, Chloroform-d) δ7.52 (d, J = 7.5Hz, 0H), 7.58–7.48 (m, 2H), 7.40–7.08 (m, 9H), 4.93 (dd, J = 11.4, 1.9 Hz,1H),4.03(dd,J=10.3,2.7Hz,1H),3.83–3.69(m,3H),3.45–3.27(m,1H),2.89(dt,J=13.0,2.3Hz,1H) ,2.77–2.40(m,4H),2.28(s,3H); 13 C NMR (101MHz, CDCl 3 )δ170.52, 137.11, 136.08, 135.47, 130.54, 129.00, 128.51, 127.59, 127.54, 126.96, 126.57, 62.07, 61.71, 57.41, 57.36, 47.95, 30.14, 1...

Embodiment 3

[0031]

[0032] Add 2-(m-methylphenyl)pyrazolidine 3-ketoylide (0.125mmol) and N-methoxy-N-trimethylsilylbenzylamine (Ⅲ) (0.125mmol) into a 15mL reaction tube, Then add CH 2 Cl 2 (1 mL) and trifluoroacetic acid (0.0125 mmol). Then N-methoxy-N-trimethylsilylbenzylamine (Ⅲ) (0.375 mmol) was added in batches, and the reaction system was stirred at 10° C. for 72 h until the reaction was complete. The reaction solution was spin-dried and directly purified by silica gel column chromatography (eluent: petroleum ether / ethyl acetate=1 / 9) to obtain a white solid. 67% yield, a white solid. 1 H NMR (400MHz, Chloroform-d) δ7.52 (d, J = 7.6Hz, 1H), 7.39–7.32 (m, 3H), 7.30–7.11 (m, 5H), 4.93 (dd, J = 11.4, 1.9 Hz,1H),4.03(dd,J=10.4,2.7Hz,1H),3.86–3.72(m,3H),3.42–3.31(m,1H),2.93–2.85(m,1H),2.75–2.42( m,4H),2.28(s,3H); 13 C NMR (101MHz, CDCl 3 )δ170.52, 137.10, 136.07, 135.47, 130.53, 129.00, 128.51, 127.58, 127.53, 126.96, 126.56, 62.08, 61.71, 57.41, 57.35, 47.95, 30.14, 19.41; ma...

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Abstract

The invention discloses a tetralin pyrazolone triazine compound as well as a preparation method and application thereof. The tetralin pyrazolone triazine compound is shown in the general formula (I). The preparation method comprises the following steps: the compounds shown in the general formulas (II) and (III) are mixed in a solvent to react under the catalysis of protonic acid or lewis acid so as to obtain the compound as shown in the general formula (I). According to the invention, a simple and practical novel method is provided for preparing a tetralin pyrazolone derivative. The prepared compound is not reported in documents and is a novel compound. The preparation method provided by the invention is an acid catalysis cycloaddition method, the reaction has molecular economy, the catalyst is protonic acid or lewis acid, application of transition metal is avoided, and the product is prevented from heavy metal pollution risk; an expensive phosphine catalyst is not required, and the cost is low.

Description

technical field [0001] The invention belongs to the technical field of organic compound preparation, and specifically relates to a tetrahydropyrazolone triazine derivative, a preparation method and application thereof. Background technique [0002] The tetrahydropyrazolone structure is an important skeleton in the development of new drugs and pesticides, and its derivatives exhibit a wide range of biological activities, such as non-steroidal painkillers C1, antidiabetic drugs C2, fungicides C3, herbicides C4 , insecticide C5, antibiotic C6, etc. Some compounds have entered the market as FDA drugs and pesticides. Therefore, the efficient preparation method of tetrahydropyrazolone derivatives has attracted much attention, especially how to efficiently and economically obtain tetrahydropyrazolone derivatives with molecular diversity. [0003] [0004] The intermolecular cycloaddition reaction is one of the most effective methods for preparing heterocyclic compounds. Since t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04A01N43/90A01P5/00A01P1/00A01P3/00
CPCA01N43/90C07D487/04
Inventor 那日松李洪连刘佳王长青田佳轩李文明何睿刘向阳张猛蒋世军孙铖
Owner HENAN AGRICULTURAL UNIVERSITY
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