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Synthesis method of (E)-configuration alkene ester triazole compound

An enestertriazole and synthesis method technology, applied in the direction of steroids, organic chemical methods, organic chemistry, etc., can solve the problems of harsh reaction conditions, complex starting materials, and long synthetic routes, and achieve simple operation and high-level steps Economical, substrate range, wide range of effects

Active Publication Date: 2018-12-14
SHAANXI NORMAL UNIV
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Problems solved by technology

[0004] 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, and harsh reaction conditions, and to provide a kind of raw materials that are easy to obtain, easy to operate, and efficiently synthesized by tandem reactions and photoreactions ( E)-Methods for configuring enester triazole compounds

Method used

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  • Synthesis method of (E)-configuration alkene ester triazole compound
  • Synthesis method of (E)-configuration alkene ester triazole compound
  • Synthesis method of (E)-configuration alkene ester triazole compound

Examples

Experimental program
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Embodiment 1

[0019] Synthesis of (E)-O-methyl-3-(1-cyclohexyl-1H-1,2,3-triazol-4-yl)acrylate with the following structural formula

[0020]

[0021] 1. Add 176mg (1.0mmol) 5-bromo-2-furanmethanol, 150mg (1.2mmol) cyclohexyl azide, 152mg (1.5mmol) triethylamine to a 25mL round bottom flask, then add 5mL dry dichloromethane As the reaction solvent, mix well and stir for 1min, then place the reaction solution in an ice-water bath, add 1.1mL 1mol / L SnCl 4 dichloromethane solution and 48 mg (1.5 mmol) methanol, the reaction mixture was slowly warmed to room temperature, and monitored by thin-layer chromatography. After the reaction was complete, the reactant was quenched with saturated aqueous sodium bicarbonate solution, then diluted with 20 mL of dichloromethane, the organic phase was separated, and the aqueous phase was transferred to a separatory funnel and extracted with dichloromethane (10 mL×2 times). , combined the organic layers, the organic phase was washed twice with 10mL saturat...

Embodiment 2

[0024]Synthesis of (E)-O-isopropyl-3-(1-cyclohexyl-1H-1,2,3-triazol-4-yl)acrylate with the following structural formula

[0025]

[0026] In this example, the methanol used in Example 1 was replaced with equimolar isopropanol, and the other steps were the same as in Example 1 to obtain (E)-O-isopropyl-3-(1-cyclohexyl-1H-1 , 2,3-triazol-4-yl) acrylate 60mg, its total yield is 56%, and the structural characterization data is: 1 H NMR (600MHz, CDCl 3 )δ7.67(s,1H),7.63(d,J=16.0Hz,1H),6.59(d,J=16.0Hz,1H),5.17-5.06(m,1H),4.49-4.41(m,1H ),2.21(dd,J=13.5,1.9Hz,2H),1.92(dd,J=11.0,3.0Hz,2H),1.75(ddd,J=15.9,9.4,3.2Hz,3H),1.46(d, J=13.3Hz, 2H), 1.28(d, J=6.3Hz, 7H); 13 C NMR (151MHz, CDCl 3 )δ166.25, 143.15, 132.42, 120.80, 120.13, 67.86, 60.23, 33.47, 25.06, 25.01, 21.87; HRMS (ESI) C 14 h 21 N 3 NaO 2 [M+Na] + : The theoretical value is 286.1531, and the measured value is 286.1532.

Embodiment 3

[0028] Synthesis of (E)-O-2-butynyl-3-(1-cyclohexyl-1H-1,2,3-triazol-4-yl)acrylate with the following structural formula

[0029]

[0030] In this example, the methanol used in Example 1 was replaced with equimolar homopropargyl alcohol, and the other steps were the same as in Example 1 to obtain (E)-O-2-butynyl-3-(1-cyclohexyl- 40 mg of 1H-1,2,3-triazol-4-yl)acrylate, the total yield is 31%, and the structural characterization data are: 1 H NMR (600MHz, CDCl 3 )δ7.68(dd, J=9.2,6.8Hz,2H),6.65(d,J=16.0Hz,1H),4.46(s,1H),4.30(t,J=6.8Hz,2H),2.59( td,J=6.8,2.6Hz,2H),2.22(d,J=11.5Hz,2H),1.93(d,J=13.8Hz,2H),1.77-1.70(m,3H),1.46(d,J =13.2Hz, 2H), 1.32-1.23(m, 2H); 13 C NMR (151MHz, CDCl 3 )δ166.40, 142.96, 133.33, 121.07, 118.93, 80.03, 69.91, 62.21, 60.27, 33.48, 25.07, 25.02, 19.02; HRMS (ESI) C 15 h 19 N 3 NaO 2 [M+Na] + : The theoretical value is 296.1735, and the measured value is 296.1736.

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Abstract

The invention discloses a synthesis method of an (E)-configuration alkene ester triazole compound. The structural formula of the compound is shown as the follows. According to the synthesis method, firstly, high-functionalization (Z)-configuration alkenyl ester triazole is synthesized through a one-pot three-component reaction by utilizing an azide, an alcohol and 5-bromo-2-furfuryl alcohol underthe action of Lewis acid, and then the (Z)-configuration alkenyl ester triazole is converted to the (E)-configuration alkene ester triazole under a condition of ultraviolet illumination. The method has the advantages that the operation is simple, the substrate selection range is wide, and a series of (Z)-configuration alkenyl ester triazole compounds can be converted into (E)-configuration alkeneester triazole compounds through photoreactions.

Description

technical field [0001] The invention relates to a method for synthesizing a class of (E)-configuration enester triazole compounds. Background technique [0002] Nitrogen-containing heterocyclic compounds represented by 1,2,3-triazole are a very important class of compounds with good biological activity and structural diversity. In particular, the enestertriazole compound formed by conjugating 1,2,3-triazole with α,β-unsaturated ester group has been used in the research and development of new anticancer drugs. In the traditional multi-step organic synthesis process, a large number of processes such as separation and purification are required, and the steps are numerous and the efficiency is low. Therefore, it is of great significance to reduce the waste of manpower and material resources in the process of organic synthesis by starting from simple and easy-to-obtain raw materials, developing cascade reactions and multi-component reactions with high step economy, and then real...

Claims

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Application Information

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IPC IPC(8): C07D249/04C07D249/06C07J43/00
CPCC07B2200/09C07D249/04C07D249/06C07J43/003
Inventor 俞斌勋杨恒拓苟婧
Owner SHAANXI NORMAL UNIV
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