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Method for synthesizing 3-aryl thiopropionamide derivative

A technology of arylthiopropionamide and arylpropyne derivatives, which is applied in the field of preparation of 3-arylthiopropionamide derivatives, can solve few problems such as thioamides, and achieve universal application of strong substrates Sexuality, development promotion and emission reduction effects

Active Publication Date: 2019-12-20
WENZHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, even for the Willgerodt-Kindler reaction, there are few reports for the synthesis of thioamides with longer alkyl chains

Method used

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  • Method for synthesizing 3-aryl thiopropionamide derivative
  • Method for synthesizing 3-aryl thiopropionamide derivative
  • Method for synthesizing 3-aryl thiopropionamide derivative

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preparation example Construction

[0014] The invention discloses a three-component one-pot method for synthesizing 3-arylthiopropionamide derivatives of aryl propyne derivatives, elemental sulfur and formamide, comprising the following steps: aryl propyne substrate, Alkali is used as a promoter, and elemental sulfur is used as a sulfur source. In the solvent formamide, at 100-120 ° C, the reaction is stirred for 12 hours. The chemical reaction formula is as follows:

[0015]

[0016] The -Ar is phenyl, 4-methylphenyl, 3-methylphenyl, 2-methylphenyl, 4-ethylphenyl, 4-tert-butylphenyl, 4-methoxybenzene Base, 3-methoxyphenyl, 3-fluorophenyl, 3-chlorophenyl, 3-bromophenyl, 4-trifluoromethylphenyl, 4-phenylphenyl, 1-naphthyl, 2 - a kind of in thienyl;

[0017] The -R, -R' is one of hydrogen, methyl, ethyl, piperidinyl, and morpholinyl;

[0018] The -LG is one of N-methyl, N-methylphenyl, N,N-dimethyl, piperidinamine, morpholinamine, hydroxyl, phenoxy, phenylmercapto and chlorine.

[0019] After the reaction w...

specific Embodiment 1

[0020] Specific embodiment one: with 41.4 milligrams (0.2mmol) N-(3-phenylprop-2-yn-1-yl)aniline, 61.4 milligrams (0.24mmol) elemental sulfur, 34.8 milligrams (3 equivalents) potassium fluoride, Add 2 mL of solvent N,N-dimethylformamide. The reaction was stirred at 120°C for 12 hours. After the reaction was cooled, the mixture was poured into ethyl acetate and washed with brine (2×15 mL). After extracting the aqueous layer with ethyl acetate, the combined organic layers were washed with anhydrous Na 2 SO 4 Dry, filter, and use a rotary evaporator to remove the solvent from the filtrate to obtain a residue, conduct column separation on the residue through a silica gel column, and rinse with the eluent, collect the effluent containing the target product, combine the effluent and vacuum Concentrate to remove the solvent to obtain the target product. The residue was washed through a silica gel column with an eluent prepared with petroleum ether and ethyl acetate at a volume ra...

specific Embodiment 2

[0021] Specific embodiment two: 44.2 milligrams (0.2mmol) N-(3-(p-tolyl) prop-2-yn-1-yl) aniline, 61.4 milligrams (0.24mmol) elemental sulfur, 34.8 milligrams (3 equivalents) fluorine Potassium chloride was added to 2 ml of solvent N,N-dimethylformamide. The reaction was stirred at 120°C for 12 hours. After the reaction was cooled, the mixture was poured into ethyl acetate and washed with brine (2×15 mL). After extracting the aqueous layer with ethyl acetate, the combined organic layers were washed with anhydrous Na 2 SO 4 Dry, filter, and use a rotary evaporator to remove the solvent from the filtrate to obtain a residue, conduct column separation on the residue through a silica gel column, and rinse with the eluent, collect the effluent containing the target product, combine the effluent and vacuum Concentrate to remove the solvent to obtain the target product. The residue was washed through a silica gel column with an eluent prepared with petroleum ether and ethyl aceta...

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Abstract

The invention relates to a method for synthesizing a 3-aryl thiopropionamide derivative. The method comprises the following step: by taking an aryl allylene derivative as a substrate, an alkali as a promoter and elemental sulfur as a sulfur source, performing a stirring reaction for 12 hours in a formamide solvent at 100-120 DEG C. The method adopts the elemental sulfur which is odorless, easy toobtain and low in price as the sulfur source, and has the advantages of being simple and easy in raw material obtaining, simple in reaction operation, mild in condition, wide in substrate universality, high in yield and good in functional group compatibility.

Description

technical field [0001] The invention relates to a preparation method of 3-arylthiopropionamide derivatives. Background technique [0002] Thioamide derivatives have many biological and pharmaceutical activities, and are often used as DNA gyrase inhibitors, cell-permeable and plasma-stable peptidomimetic inhibitors and non-nucleoside reverse transcriptase inhibitors (J.Med.Chem . 2011, 54, 2207-2224; J. Med. Chem. 2011, 54, 1333-1346; Med. Chem. 2007, 3, 513-519). Furthermore, thioamides are very useful synthetic starting materials for the synthesis of various sulfur-containing heterocycles, such as thieno[2,3-b]indole, thiazole and benzothiazole (Adv.Synth.Catal.2017,359,4300 -4304; Org. Lett. 2011, 13, 1718-1721; Org. Lett. 2016, 18, 356-359). Traditionally, the sulfidation of carboamides has been carried out using Lawesson's reagent or phosphorus pentasulfide, but these raw materials are less economical (Org. Lett. 2003, 5, 721-724; Chem. Commun. 2009, 46, 7122-7124). T...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C327/44
CPCC07C327/44
Inventor 张小红徐宏辉张兴国
Owner WENZHOU UNIVERSITY
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