Preparation method of thiamine 1,4-naphthoquinone compound

A technology of a compound, naphthoquinone, applied in the field of preparation of thiamined 1,4-naphthoquinone compound, can solve problems such as inability to realize one-step reaction, poor reaction adaptability, etc., and achieve mild, simple and economical reaction conditions good sex effect

Inactive Publication Date: 2019-04-05
ZHENGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the one-step reaction cannot be realized, and the reaction adaptability is not good
The method disclosed in the present invention for the one-step efficient synthesis of naphthoquinone thiamin

Method used

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  • Preparation method of thiamine 1,4-naphthoquinone compound
  • Preparation method of thiamine 1,4-naphthoquinone compound
  • Preparation method of thiamine 1,4-naphthoquinone compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] The preparation method of thiamined 1,4-naphthoquinone compound, the steps are as follows:

[0025] In a 25 mL reaction tube, cuprous iodide (20 mol%), 0.5 mmol of 1,4-naphthoquinone, 2 mL of solvent DMF, 0.5 mmol of p-methylbenzenethiol, and 1.75 mmol of tetrahydropyrrole were added, and the mixture was stirred in an oxygen atmosphere. , the reaction temperature was controlled to be 100 °C, and after 10 hours of reaction, silica gel column chromatography was used to separate the final product, and the yield of the final product was 80% based on the molar weight of 1,4-naphthoquinone as 100%.

[0026] The specific results are as follows:

[0027]

[0028] 1 H NMR (400 MHz, Chloroform- d ) δ 8.10 (dd, J = 7.7, 1.3 Hz, 1H), 7.93(dd, J = 7.7, 1.3 Hz, 1H), 7.69 (td, J = 7.5, 1.4 Hz, 1H), 7.60 (td, J = 7.5,1.3 Hz, 1H), 7.05 (q, J = 8.3 Hz, 5H), 3.94 – 3.85 (m, 4H), 2.28 (s, 3H), 1.85 – 1.77 (m, 4H). 13 C NMR (101 MHz, Chloroform- d ) δ 184.38, 180.28, 155.6...

Embodiment 2

[0030] The preparation method of thiamined 1,4-naphthoquinone compound, the steps are as follows:

[0031] In a 25 mL reaction tube, cuprous iodide (20 mol%), 0.5 mmol of 1,4-naphthoquinone, 2 mL of solvent DMF, 0.5 mmol of p-ethylbenzenethiol, 1.75 mmol of tetrahydropyrrole were added, and the mixture was stirred in an oxygen atmosphere. The reaction temperature was controlled to be 100 °C, and after 10 hours of reaction, the final product was obtained by separation by silica gel column chromatography, and the yield of the final product was 65% based on the molar amount of 1,4-naphthoquinone being 100%.

[0032] The specific results are as follows:

[0033]

[0034] 1 H NMR (400 MHz, Chloroform- d ) δ 8.11 (dd, J = 7.7, 1.3 Hz, 1H), 7.94(dd, J = 7.6, 1.3 Hz, 1H), 7.70 (td, J = 7.5, 1.4 Hz, 1H), 7.61 (td, J = 7.5,1.3 Hz, 1H), 7.13 – 7.04 (m, 4H), 3.97 – 3.85 (m, 4H), 2.58 (q, J = 7.6 Hz, 2H), 1.87 – 1.75 (m, 4H), 1.20 (t, J = 7.6 Hz, 3H). 13 C NMR (101 MHz, ...

Embodiment 3

[0036] The preparation method of thiamined 1,4-naphthoquinone compound, the steps are as follows:

[0037] In a 25 mL reaction tube, add cuprous iodide (20 mol%), 0.5 mmol of 1,4-naphthoquinone, 2 mL of solvent DMF, 0.5 mmol of 2-chlorobenzenethiol, 1.75 mmol of tetrahydropyrrole, and stir in an oxygen atmosphere. , the reaction temperature was controlled to be 100°C, and after 10 hours of reaction, the final product was obtained by silica gel column chromatography separation, and the yield of the final product was 65% based on the molar amount of 1,4-naphthoquinone being 100%.

[0038] The specific results are as follows:

[0039]

[0040] 1 H NMR (400 MHz, Chloroform- d ) δ 8.09 (dd, J = 7.8, 1.2 Hz, 1H), 7.93(dd, J = 7.6, 1.3 Hz, 1H), 7.69 (td, J = 7.6, 1.4 Hz, 1H), 7.61 (td, J = 7.6,1.4 Hz, 1H), 7.30 (dd, J = 7.8, 1.4 Hz, 1H), 7.09 (td, J = 7.6, 1.5 Hz, 1H), 7.01 (td, J = 7.6, 1.7 Hz, 1H), 6.93 (dd, J = 7.8, 1.6 Hz, 1H), 3.96 – 3.87(m, 4H), 1.90 – 1.79...

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Abstract

The invention uses naphthoquinone, amine and mercaptan as raw materials, and provides a preparation method of a thiamine 1,4-naphthoquinone compound. The synthesis method has mild reaction conditions,oxygen is used as an oxidant under the condition of copper catalysis, and multiple thiamine 1,4-naphthoquinone compounds can be synthesized through a one-step reaction, and thus the method provides an efficient and practical synthesis method which is simple, convenient and efficient, cheap and easily-available in raw materials and catalysts, wide in adaptability, and has good application value and market prospect.

Description

technical field [0001] The invention relates to the field of chemical synthesis, in particular to a preparation method of a thioaminated 1,4-naphthoquinone compound. Background technique [0002] Thiaminated 1,4-naphthoquinone compounds are an important class of organic compounds that are widely used in organic synthetic chemistry, biochemistry and medicinal chemistry due to their unique biological activity and antibacterial properties. Generally, thiamined 1,4-naphthoquinone compounds can be synthesized by nucleophilic substitution reaction of naphthoquinone halides (eg: RSC Adv., 2014, 4, 12441-12447. Acc Chem Res, 2015, 48, 1756 -1766.), and this reaction uses halogenated naphthoquinones as starting materials and reacts with thiols and amines in two steps. Such reactions require the synthesis of halogenated naphthoquinone substrates; at the same time, the catalytic system is complex, and one-step reaction cannot be achieved; the reaction efficiency is not high, and the s...

Claims

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Application Information

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IPC IPC(8): C07D295/116
CPCC07D295/116
Inventor 陈晓岚贺帅旗曾繁林於兵屈凌波
Owner ZHENGZHOU UNIV
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