Ketene triazole compound and synthesis method thereof

A technology of enonetriazole and synthetic method, which is applied in the direction of organic chemistry, can solve the problems of complex starting materials, long synthetic routes, harsh reaction conditions, etc., and achieves a wide range of substrates, high step economy, and simple operation Effect

Inactive Publication Date: 2015-01-07
SHAANXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The technical problem to be solved by the present invention is to overcome the shortcomings of existing methods such as complex starting materials, long synthetic routes, low reaction yields, harsh reaction conditions, etc., and synthesize multifunctional multi-substituted complex enonetriazole compounds, and for the Compounds provide a simple and efficient method for the synthesis of tandem reactions

Method used

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  • Ketene triazole compound and synthesis method thereof
  • Ketene triazole compound and synthesis method thereof
  • Ketene triazole compound and synthesis method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0018] Taking (E)-4-(1-benzyl-1 hydrogen-1,2,3-triazol-4-yl)but-3-en-2-one as an example with the following synthetic structural formula, the raw materials used and their synthesis Methods as below:

[0019]

[0020] Add 112mg (1.0mmol) of 5-methyl-2-furylmethanol and 146mg (1.1mmol) of benzyl azide into 5mL of dichloromethane, place in a -20°C ice-salt bath, stir, and then dropwise add 1.1mL of 1mol / L TiCl 4 (1.1mmol) of dichloromethane solution, stirred at room temperature for 30 minutes after the dropwise addition, and the reaction mixture was washed with saturated NaHCO 3 Quenched, then diluted with 20mL ether, washed with saturated brine (2×5mL), extracted with ether (2×10mL), the organic phase was dried over anhydrous sodium sulfate and filtered, concentrated and washed with petroleum ether and ethyl acetate The mixed solution with a volume ratio of 1:1 was used as the eluent for column chromatography to obtain (E)-4-(1-benzyl-1hydrogen-1,2,3-triazol-4-yl)butan-3 ...

Embodiment 2

[0022] In Example 1, the TiCl used 4 with equimolar AlCl 3 Replacement, other steps are the same as in Example 1 to obtain (E)-4-(1-benzyl-1 hydrogen-1,2,3-triazol-4-yl)but-3-en-2-one, which The yield was 46%.

Embodiment 3

[0024] In Example 1, the TiCl used 4 with equimolar FeCl 3 Replacement, the reaction time was extended to 120 minutes, and other steps were the same as in Example 1 to obtain (E)-4-(1-benzyl-1 hydrogen-1,2,3-triazol-4-yl)butan-3- En-2-one in 51% yield.

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Abstract

The invention discloses a ketene triazole compound and a synthesis method thereof. The structural formula of the compound is disclosed in the specification. Alkyl or aryl azide and various substituted 2-furancarbinol used as initial raw materials are subjected to Lewis-acid-promoted [3+2]-cycloaddition/furan ring opening cascade reaction to generate a (E)-configuration 1,2,3-triazole and ketene/aldehyde conjugated skeleton structure. The method is simple to operate, the reagent is the low-cost Lewis acid, and the substrate has wide application range; and thus, the method can be used for synthesizing a series of high-functional-group substituted complex ketene triazoles, and has the advantages of high economical efficiency of steps, diversified product structures and stereospecificity of (E)-configuration.

Description

technical field [0001] The invention specifically relates to a ketene triazole compound and a synthesis method thereof. Background technique [0002] For drug discovery and the development of cell signaling molecular probes, rapid and reliable synthesis of heterocyclic compounds has become one of the core parts in these fields. 1,2,3-triazoles exhibit unique advantages, and compounds with this type of structure have been proven to have a broad spectrum of biological activities. They have been widely used in organic synthesis, biochemistry and materials science. Among them, the enonetriazole skeleton structure represents an important class of small molecular compounds. Due to its high biocompatibility, this kind of backbone has been studied to have an inhibitory effect on histone deacetylase (HDAC). Histone deacetylase inhibitors inhibit the proliferation of tumor cells and induce cell differentiation and (or) apoptosis by increasing the degree of acetylation of intracellu...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D249/04
CPCC07D249/04C07D249/06
Inventor 俞斌勋郭家伟苟婧
Owner SHAANXI NORMAL UNIV
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