Preparation method of aryl thioamides

A technology of aryl thioamides and amide solvents, which is applied in the field of preparation of aryl thioamide compounds, can solve the problems of low yield, complex structure of reactants, harsh reaction conditions, etc., and achieve simple process and applicable scope of substrates wide effect

Active Publication Date: 2018-06-22
SHANGQIU NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these synthetic methods generally have many problems, such as harsh reaction conditions, complex structures of reactants, and low yields, which limit their application.

Method used

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  • Preparation method of aryl thioamides
  • Preparation method of aryl thioamides
  • Preparation method of aryl thioamides

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Base screening test: Different bases promote the three-component reaction involving aromatic alkynes, resulting in different yields.

[0025] Take phenylacetylene (0.4mmol), elemental sulfur (9.6mmol), alkali (1.2mmol), add 2mL N, N-dimethylformamide to make a mixture, place the mixture in a 10mL pressure-resistant tube and seal it, at 115°C After heating in an oil bath for 20 h, cool to room temperature and add 25 mL of water to quench, the aqueous phase was extracted with dichloromethane (10 mL x 3), the organic phases were combined, and anhydrous MgSO 4 After drying and concentration, add 30 mL of methanol, filter and concentrate, and then separate by thin-layer chromatography to obtain the target product A.

[0026]

[0027] Different bases promote the three-component reaction involving aromatic alkynes, and different yields are obtained. The experimental results are as follows:

[0028]

Embodiment 2

[0030] The preparation method of the aryl thioamide compound A of following structure:

[0031]

[0032] Take phenylacetylene (0.4mmol), elemental sulfur (9.6mmol), anhydrous potassium phosphate (1.2mmol), add 2mL N,N-dimethylformamide to make a mixture, and place the mixture in a 10mL pressure-resistant tube Sealed, heated in an oil bath at 115°C for 20h, cooled to room temperature and quenched with 25mL of water, the aqueous phase was extracted with dichloromethane (10mL x 3), the organic phase was combined, anhydrous MgSO 4 After drying and concentration, add 30 mL of methanol, filter and concentrate, and then separate by thin-layer chromatography to obtain 56 mg of the target product A as a yellow solid, with a yield of 84%. NMR characterization: 1 H NMR (400MHz, CDCl 3 )δ7.31–7.28(m,5H),3.55(s,3H),3.11(s,3H); 13 C NMR (CDCl 3 , 100MHz) δ200.9, 143.3, 128.6, 128.3, 125.7, 44.2, 43.2.

Embodiment 3

[0034] The only difference between this example and Example 2 is that the solvent used was N,N-dimethylacetamide (2 mL), and 44 mg of the target product A was obtained with a yield of 66%.

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Abstract

The invention belongs to the technical field of organic synthesis and discloses a preparation method of aryl thioamides. According to the method, corresponding aryl thioamides are generated from aromatic alkynes, elemental sulfur and amides as raw materials through a reaction of the three components under alkaline condition without catalysis by transition metals. The synthetic system has a wide application range and is compatible with terminal alkynes and internal alkynes, and is also compatible with formamide, acetamide and propionamide derivatives. The method has the advantages that raw materials are economical and easily available, the process is simple, the substrate application range is wide, the yield is high, and the method is suitable for industrial popularization and application.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a preparation method of an aryl thioamide compound. Background technique [0002] Compared with alkylthioamides, arylthioamides are widely used intermediates in fields such as heterocyclic chemistry, protein chemistry, medicinal chemistry and materials science (K.Sestanj et al.J.Med.Chem . 1984, 27, 255; S.R. Stauffer et al. Bioorg. Med. Chem. 2000, 8, 1293; J. Matysiak et al. Eur. J. Med. Chem. 2000, 35, 393). In the prior art, some synthetic methods have successfully prepared aryl thioamide compounds, such as traditional synthetic methods such as the thiolation of aryl amide, the Willgerodt-Kindler reaction and the three-component reaction of step economy (T.B.Nguyen et al. al.Org.Lett.2012,14,4274; X.G.Zhou et al.Adv.Synth.Catal.2013,355,3141; K.N.Singh et al.Org.Lett.2014,16,3624;X.F.Jiang et al.Org. Lett.2016, 18, 340), wherein the three-component rea...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C327/48C07D295/104
Inventor 许凯刘澜涛王涛李峰刘双张安安孟团结赵文献
Owner SHANGQIU NORMAL UNIVERSITY
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