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One-pot synthetic method for 1,2,3-triazole compounds

A synthesis method and compound technology, applied in the direction of organic chemistry, etc., can solve problems such as the reduction of reaction efficiency, and achieve the effects of high safety, simple operation and mild conditions

Active Publication Date: 2013-04-24
THE CITY VOCATIONAL COLLEGE OF JIANGSU
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

And if the starting material is a nitrobenzaldehyde compound, it is easy to self-condense in the reduction process, resulting in the problem of reduced reaction efficiency

Method used

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  • One-pot synthetic method for 1,2,3-triazole compounds
  • One-pot synthetic method for 1,2,3-triazole compounds
  • One-pot synthetic method for 1,2,3-triazole compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Preparation of (1-(4-bromophenyl)-4-hydroxymethyl)-1,2,3-triazole

[0032]

[0033] Add 201mg (1mmol) of 4-bromonitrobenzene, 130mg (2mmol) of sodium azide, 56mg (1mmol) of propynyl alcohol, 40mg (0.2mmol) of sodium ascorbate, and 38mg (0.2mmol) of cuprous iodide to the round bottom flask. ), adding 20mL of hexamethylphosphoric triamide, heating to 60°C, stirring and reacting for 8 hours under the protection of nitrogen. After the reaction was detected by TLC, the insoluble matter was removed by suction filtration, 100 mL of ethyl acetate was added, washed twice with saturated brine, and the organic phase was dried with a desiccant. The desiccant was removed by suction filtration, and the filtrate was spin-dried. The obtained product was purified by silica gel column chromatography to obtain 272 mg of a light yellow solid with a yield of 90.9%.

[0034] The data are characterized as follows:

[0035] 1 H NMR (500MHz, DMSO-d6): δ4.60(s, 2H), 7.78-7.89(m, 4H), 8.73...

Embodiment 2

[0037] Preparation of (1-(4-chlorophenyl)-4-ethoxycarbonyl)-1,2,3-triazole

[0038]

[0039] Add 157mg (1mmol) of 4-chloronitrobenzene, 163mg (2.5mmol) of sodium azide, 117mg (1.2mmol) of ethyl propiolate, 99mg (0.5mmol) of sodium ascorbate, and cuprous iodide to the round-bottomed flask. 96mg (0.5mmol), add 30mL hexamethylphosphoric triamide, heat to 100°C, stir and react for 5 hours under nitrogen protection. After the reaction was detected by TLC, the insoluble matter was removed by suction filtration, 100 mL of ethyl acetate was added, washed twice with saturated brine, and the organic phase was dried with a desiccant. The desiccant was removed by suction filtration, and the filtrate was spin-dried. The obtained product was purified by recrystallization to obtain 225 mg of off-white solid, with a yield of 88.2%.

[0040] The data are characterized as follows:

[0041] 1 H NMR(500MHz,DMSO-d6):δ9.51(s,1H),8.03(d,J=8.4,2H),7.70(d,J=8.4,2H),4.36(q,J=7.0,2H ),1.34(t,J=7...

Embodiment 3

[0043] Preparation of (1-(4-ethoxycarbonyl)-4-hydroxymethyl)-1,2,3-triazole

[0044]

[0045] Add 195 mg (1 mmol) of ethyl 4-nitrobenzoate, 260 mg (4 mmol) of sodium azide, 62 mg (1.1 mmol) of propynyl alcohol, 59 mg (0.3 mmol) of sodium ascorbate, and 75 mg of copper sulfate pentahydrate into the round bottom flask (0.3mmol), add 40mL of hexamethylphosphoric triamide, heat to 50°C, stir and react for 10 hours under the protection of nitrogen. After the reaction was detected by TLC, the insoluble matter was removed by suction filtration, 120 mL of ethyl acetate was added, washed twice with saturated brine, and the organic phase was dried with a desiccant. The desiccant was removed by suction filtration, and the filtrate was spin-dried. The obtained product was purified by recrystallization to obtain 209 mg of off-white solid, with a yield of 84.7%. The data are characterized as follows:

[0046] 1H NMR(500MHz,DMSO-d6):δ8.82(s,1H),8.43-7.76(m,4H),4.64(d,J=5.4Hz,2H),4.40(...

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Abstract

The invention provides a one-pot method for synthesizing 1,2,3-triazole compounds, and belongs to the technical field of organic synthesis. According to the one-pot synthetic method for the 1,2,3-triazole compounds, nitrobenzene compounds and alkyne compounds serve as starting materials, and a plurality of the 1,2,3-triazole compounds are synthesized conveniently in a one-pot mode under the catalysis of copper. The 1,2,3-triazole compounds synthesized with the one-pot synthetic method are important intermediates for drug synthesis, and have very important application prospects in the fields including biomedicine, medicines and the like. Certain components are already widely used for clinics. The method adopts one-pot preparation, so that diazotization reaction is avoided, organic azides are not directly used, and the one-pot synthetic method for the 1,2,3-triazole compounds is high in safety, simple in operation, mild in conditions, low in cost and easy to use for industrial production and has good application prospects.

Description

technical field [0001] The invention provides a method for synthesizing 1,2,3-triazole compounds, in particular to a method for synthesizing 1,2,3-triazole compounds in one pot, and belongs to the technical field of organic synthesis. Background technique [0002] 1,2,3-Triazole compounds are a very important class of compounds with aromatic ring stability and good biocompatibility [1] , the pharmacophore of different substrates is linked into a molecule through the triazole ring, and its product can improve the binding ability to the biological target through hydrogen bonding and dipole interaction, and has lower toxicity than imidazole [2] . Such compounds are widely used in biomedicine, pesticides, materials, catalysis and other fields. There are many triazole derivatives as antibacterial [3] ,Antitumor [4] , anti-inflammatory [5] , antihypertensive [6] and other drugs are widely used clinically. [0003] 1,2,3-Triazole compounds usually use nitrobenzene compounds ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D249/06
Inventor 刘霞
Owner THE CITY VOCATIONAL COLLEGE OF JIANGSU
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