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1,2,3-triazole 1,3-nitrogen heterocyclic compound, producing method and application of the same

A technology for diazide heterocycles and compounds, which is applied to 1,2,3-triazolo 1,3-diazaheterocycle compounds and the fields of their preparation and application, achieves high yield, mild reaction conditions and good biological activity Effect

Inactive Publication Date: 2010-05-12
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But so far, most of the research on triazole fungicides has focused on 1,2,4-triazole compounds, and there are relatively few studies on 1,2,3-triazole compounds. Isoxazole as a representative of a few

Method used

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  • 1,2,3-triazole 1,3-nitrogen heterocyclic compound, producing method and application of the same
  • 1,2,3-triazole 1,3-nitrogen heterocyclic compound, producing method and application of the same
  • 1,2,3-triazole 1,3-nitrogen heterocyclic compound, producing method and application of the same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Example 1, Synthesis of 4-(4-fluorobenzoyl)-[1,2,3]triazol[1,5-e]tetrahydroimidazole (in formula I, n=1, Y=NH, R 1 =4-fluorophenyl) (Compound I-a)

[0034] In a 50 ml round bottom flask were added dry acetonitrile (20 ml), 2-(4-fluorobenzoyl)methylenetetrahydroimidazole (1.0 mmol) and p-toluenesulfonyl azide (1.0 mmol mol), heated under electromagnetic stirring, and now the raw material was completely dissolved, and the reaction system was a reddish-brown solution. TLC detection continued to react until the raw material disappeared completely, and there was only one product point. The solvent was distilled off under reduced pressure, and the crude brown-yellow solid product was recrystallized from a common organic solvent to obtain a light yellow crystal, which was the target product 4-(4-fluorobenzoyl)-[1,2,3]triazole[ 1,5-e]tetrahydroimidazole (compound I-a), yield: 81.3%; product melting point: 199-200°C.

[0035]Proton NMR spectrum (deuterated chloroform as solven...

Embodiment 2

[0040] Example 2, Synthesis of 4-(4-trifluoromethylbenzoyl)-[1,2,3]triazol[1,5-e]tetrahydroimidazole (in formula I, n=1, Y= NH, R 1 =4-trifluoromethylphenyl) (Compound I-b)

[0041] In a 50 ml round bottom flask, add dry acetonitrile as solvent, equivalent 2-(4-trifluoromethylbenzoyl) methylenetetrahydroimidazole and p-toluenesulfonyl azide, stir under electromagnetic The raw material is completely dissolved under heating, and the reaction system is a reddish-brown solution. TLC detects that the reaction continues until the raw material has completely disappeared, and there is only one product point. The solvent was distilled off under reduced pressure, and the crude brown-yellow solid product was recrystallized from a common organic solvent to obtain a light yellow crystal, which was the target product 4-(4-trifluoromethylbenzoyl)-[1,2,3] Triazolo[1,5-e]tetrahydroimidazole (I-b), yield: 80.4%; product melting point: 201-203°C.

[0042] Proton NMR spectrum (deuterated chlor...

Embodiment 3

[0047] Example 3, Synthesis of 4-(4-phenylbenzoyl)-[1,2,3]triazol[1,5-e]tetrahydroimidazole (in formula I, n=1, Y=NH, R 1 =4-phenylphenyl) (compound I-c)

[0048] Replace 2-(4-fluorobenzoyl) methylene tetrahydroimidazole in embodiment 1 with 2-(4-phenylbenzoyl) methylene tetrahydroimidazole, under the same conditions, with p-methyl phenylsulfonyl azide reacts to obtain the target product 4-(4-phenylbenzoyl)-[1,2,3]triazol[1,5-e]tetrahydroimidazole (compound I-c), producing Yield: 93.0%; melting point: 239-240°C.

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Abstract

The present invention discloses a 1, 2, 3-triazole combined with 1, 3-two-nitrogen heterocyclic compound, a preparation method and application thereof. The 1, 2, 3-triazole combined with 1, 3-two-nitrogen heterocyclic compound provided by the present invention has a structure as shown in formula I; wherein, Y is O or NR'; R' is hydrogen, halogen, nitro, cyano , amino, C1-8 alkyl, C1-8 alkyla, C1-8acyl, aroyl, viscous aroyl, aryl, viscous aryl, cycloalkyl, aryl alkyl, oxa alkyl, oxa acyl, thia alkyl or thia acyl; n is equal to 1, 2 or 3; R1 is aryl, heterocyclic aryl or alkyl. In the present invention, the compound of heterocyclicketene shrinking amine category and p-methyl benzenesulfonyl azide are used as raw materials to prepare a series of 1, 2, 3-triazole combined with 1, 3-two-nitrogen heterocyclic compound of a novel structure; the synthesis is convenient; the reaction conditions are mild and easy to control; the production rate is high; the present invention is in particular suitable for industrial production; and the cost is low. The compound of the present invention has good bactericidal activity, anti-tumor activity and wide application prospects.

Description

technical field [0001] The invention relates to 1,2,3-triazole compounds and their preparation methods and applications, in particular to 1,2,3-triazolo-1,3-diaza heterocyclic compounds and their preparation methods and applications. Background technique [0002] Triazole compounds are of great value in the field of drug development and creation. Among them, many triazole fungicides occupy an important place in the big family of fungicides because of their broad-spectrum, long-term effect and high efficiency, such as carbafen, triadimefon, and leaf rust. But so far, most of the research on triazole fungicides has focused on 1,2,4-triazole compounds, and there are relatively few studies on 1,2,3-triazole compounds. Isoxazole is a representative of the few. Contents of the invention [0003] The object of the present invention is to provide a class of 1,2,3-triazolo 1,3-diaza heterocyclic compounds and a preparation method thereof. [0004] The 1,2,3-triazolo 1,3-diaza he...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/04C07D498/04A61K31/4192A61K31/5517A61K31/519A61K31/424A61K31/5383A61P31/04A61P35/00
Inventor 俞初一原学宁赵梅欣黄志镗
Owner INST OF CHEM CHINESE ACAD OF SCI