4-(benzofuran-5-yl)-2-aromatic aminothiazole and preparation method and application thereof

A technology of arylaminothiazole and arylaminothiazole salt, which is applied in the field of new compounds and their preparation, and can solve the problems of no research and development reports on application and the like

Inactive Publication Date: 2011-04-13
HUNAN UNIV
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  • Description
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  • Application Information

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Problems solved by technology

4-(Benzofuran-5-yl)-2-arylaminothiazole, its preparation method and its application as an insecticide have no research and development reports

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  • 4-(benzofuran-5-yl)-2-aromatic aminothiazole and preparation method and application thereof
  • 4-(benzofuran-5-yl)-2-aromatic aminothiazole and preparation method and application thereof
  • 4-(benzofuran-5-yl)-2-aromatic aminothiazole and preparation method and application thereof

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Experimental program
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Embodiment 14

[0021]

[0022] (1) Preparation of 2-bromo-1-(7-methoxy-2,2-dimethyl-2,3-dihydrobenzofuran-5-yl)ethanone

[0023] 0.02mol 1-(7-methoxy-2,2-dimethyl-2,3-dihydrobenzofuran-5-yl)ethanone, 80mL ethanol, stirring and reflux, add 0.04mol copper bromide in batches , reacted for 2h, filtered the reaction solution while it was hot, recovered the solvent by distillation, dissolved ethyl acetate, washed with dilute acid, filtered, washed the filtrate with water, separated, dried, and recrystallized from ethanol to obtain 2-bromo-1-(7-methoxy -2,2-Dimethyl-2,3-dihydrobenzofuran-5-yl)ethanone, yield 50.0%, melting point 90-91°C.

[0024] 2) Preparation of 4-(7-methoxy-2,2-dimethyl-2,3-dihydrobenzofuran-5-yl)-2-anilinothiazole

[0025] 2.0mmol 2-bromo-1-(7-methoxy-2,2-dimethyl-2,3-dihydrobenzofuran-5-yl)ethanone, 1.8mmol phenylthiourea, 20mL acetone, Heat and stir, react for 2 hours, the reaction solution is cooled to precipitate solid, filtered, and dried to obtain 4-(7-methoxy-2,2-...

Embodiment 24

[0027]

[0028] According to the method of Example 1, 2-bromo-1-(7-methoxy-2,2-dimethyl-2,3-dihydrobenzofuran-5-yl)ethanone and 2-tolylthio Urea reacted for 1.0h to obtain 4-(7-methoxy-2,2-dimethyl-2,3-dihydrobenzofuran-5-yl)-2-(2-methylanilino)thiazole , the yield is 92.4%, and the melting point is 146.5-147.5°C. 1 H NMR (CDCl 3 , 300MHz), δ: 1.53(s, 6H, 2×CH 3 ), 2.35(s, 3H, CH 3 ), 3.06 (s, 2H, CH 2 ), 3.95(s, 3H, OCH 3), 6.59 (s, 1H, thiazole ring 5-H), 7.10 (m, 2H, C 6 h 2 ), 7.24~7.62 (m, 4H, C 6 h 4 ); EI-MS (m / z): 367.2 (M + ).

Embodiment 34

[0030]

[0031] According to the method of Example 1, 2-bromo-1-(7-methoxy-2,2-dimethyl-2,3-dihydrobenzofuran-5-yl)ethanone and 3-methylbenzene thiourea reaction for 2.0h to obtain 4-(7-methoxy-2,2-dimethyl-2,3-dihydrobenzofuran-5-yl)-2-(3-methylanilino ) Thiazole, the yield is 87.8%, and the melting point is 177.9~178.5°C. 1 H NMR (CDCl 3 , 300MHz), δ: 1.43(s, 6H, 2×CH 3 ), 2.31 (s, 3H, CH 3 ), 3.05(s, 2H, CH 2 ), 3.83 (s, 3H, OCH 3 ), 6.77~7.58 (m, 7H, C 6 h 4 , C 6 h 2 , thiazole ring 5-H), 10.14 (s, 1H, NH); EI-MS (m / z): 367.2 (M + ).

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Abstract

The invention discloses 4-(benzofuran-5-yl)-2-aromatic aminothiazole shown as a chemical structural formula I. The preparation method of the 4-(benzofuran-5-yl)-2-aromatic aminothiazole comprises the following steps of: heating and stirring 2-halogen-1-(7-hydroxyl/alkoxyl-2,2-dimethyl-2,3-dihydrobenzofuran-5-yl) butanone and arylthiourea in acetone for reaction to obtain 4-(benzofuran-5-yl)-2-aromatic aminothiazole salt; and neutralizing the 4-(benzofuran-5-yl)-2-aromatic aminothiazole salt with stronger ammonia water to obtain the 4-(benzofuran-5-yl)-2-aromatic aminothiazole. The 4-(benzofuran-5-yl)-2-aromatic aminothiazole has high insecticidal activity and is applied to the preparation of pesticides.

Description

technical field [0001] The present invention relates to a class of novel compounds and their preparation method and application, specifically 4-(benzofuran-5-yl)-2-arylaminothiazole, its preparation method and application as insecticide. Background technique [0002] Shao Ling et al. described 4-aryl-5-triazolylthiazole-2-imine compounds, and the results of biological activity assays showed that some compounds had bactericidal activity against P. ). Michael et al. described 2-aminothiazole breast cancer drugs (Bioorg & Med.Chem.2004, 12, 1029); Jiang Fengchao et al. described 4-arylthiazole-2-imine derivatives with inhibitory activity on apoptosis (Acta Pharmacologica Sinica, 2006, 41:727). Lin et al. described the selective inhibitory effect of Schiff bases on COX-2 (Bioorg & Med Chem, 2008, 16(5):2697). He Daohang et al. described the synthesis and bactericidal activity of 4-aryl-2-(2-hydroxybenzimino)thiazole [Journal of South China University of Technology, Natural Sc...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D417/04C07D417/14A01N43/78A01P7/04A01P7/02
Inventor 罗先福胡艾希欧晓明杨林涛
Owner HUNAN UNIV
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