Thioamide compound and compounding method thereof

A technology of thioamides and synthetic methods, applied in the fields of steroids and organic chemistry, which can solve the problems of harsh substrate reaction conditions, environmental and human harm, and limited substrate universality, and achieve stereospecificity The effect of maintenance, wide substrate universality and low cost

Active Publication Date: 2016-02-03
EAST CHINA NORMAL UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In this type of method, the Lawson's reagent used is unstable, relatively expensive, low in atom economy, and has a large odor, and has various degrees of damage to the environment and the human body. The required amide must be passed through carboxylic acid (or acid chloride) in advance ) and amine condensation preparation, low step economy
In recent years, a method for preparing thioamides using the Willgerodt-Kindler reaction has been developed. This method uses sulfur as a sulfur source, and aryl aldehydes, aryl/alkyl ketones, aryl acetylenes, benzylamines, and aryl acetic

Method used

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  • Thioamide compound and compounding method thereof
  • Thioamide compound and compounding method thereof
  • Thioamide compound and compounding method thereof

Examples

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Example Embodiment

[0055] Example 1

[0056] Synthesis of compound 2a:

[0057]

[0058] Add Na in the reaction tube 2 S·9H 2 O (1.05mmol, 252mg), add isovaleraldehyde (0.3mmol, 25.8mg), N-formylpiperidine (1.5mmol, 169.5mg), pyridine (1.5mmol, 118.5mg) in water (0.6mL) and add In the reaction tube, put K 2 S 2 O 8 (0.54mmol, 146.0mg) was added to the reaction system and stirred at 100°C for 8 hours. After the reaction was detected by TLC, it was cooled to room temperature, 10mL of water was added to the system for dilution, and ethyl acetate (10mL*3) was added for extraction. Dry with anhydrous sodium sulfate, filter, concentrate, and separate by column chromatography to obtain a yellow liquid 2a (33.8mg, 61%), R f =0.55 (PE:EA=10:1); 1 HNMR(400MHz, CDCl 3 )δ4.38-4.25(m,2H),3.76-3.68(m,2H),2.80(d,J=7.3Hz,2H),2.24-2.07(m,1H),1.78-1.60(m,6H) ,1.00(d,J=6.7Hz,6H) 13 CNMR(100MHz, CDCl 3 )δ201.4,52.0,51.6,51.1,28.9,26.9,25.4,24.1,22.4; IR(film)2937,2361,1487,1440,1265,1149,1079,1002,852cm -1 ; HRMS(EI)Ca...

Example Embodiment

[0059] Example 2

[0060] Synthesis of compound 2b:

[0061]

[0062] Add Na in the reaction tube 2 S·9H 2 O (1.05mmol, 252mg), add isovaleraldehyde (0.3mmol, 25.8mg), N-formylmorpholine (1.5mmol, 172.5mg), pyridine (1.5mmol, 118.5mg) dissolved in water (0.6mL) In the reaction tube, put K 2 S 2 O 8 (0.54mmol, 146.0mg) was added to the reaction system and stirred at 100°C for 9 hours. After the reaction was detected by TLC, it was cooled to room temperature, 10mL of water was added to the system for dilution, and ethyl acetate (10mL*3) was added for extraction. Dry with anhydrous sodium sulfate, filter, concentrate, and separate by column chromatography to obtain a pale yellow liquid 2b (32.0mg, 57%), R f =0.6(PE:EA=5:1); 1 HNMR(400MHz, CDCl 3 )δ4.44-4.25(m,2H),3.86-3.62(m,6H), 2.76(d,J=7.3Hz,2H), 2.17-2.06(m,1H),0.99(d,J=6.7Hz ,6H); 13 CNMR(100MHz, CDCl 3 )δ203.2,66.6,66.5,51.6,50.4,50.1,29.1,22.3; IR(film)2961,2925,2866,1478,1431,1259,1115,1021,797cm -1 ; MS(EI)m / z(%)187(100),144...

Example Embodiment

[0063] Example 3

[0064] Synthesis of compound 2c:

[0065]

[0066] Add Na in the reaction tube 2 S·9H 2 O (1.05mmol, 252mg), dissolve 3-phenylpropanal (0.3mmol, 40.2mg), N,N-dimethylformamide (1.5mmol, 109.5mg), pyridine (1.5mmol, 118.5mg) in water (0.6mL) into the reaction tube, then K 2 S 2 O 8 (0.54mmol, 146.0mg) was added to the reaction system and stirred at 100°C for 8 hours. After the reaction was detected by TLC, it was cooled to room temperature, 10mL of water was added to the system for dilution, and ethyl acetate (10mL*3) was added for extraction. Dry with anhydrous sodium sulfate, filter, concentrate, and separate by column chromatography to obtain orange liquid 2c (48.0mg, 83%), R f =0.4(PE:EA=5:1); 1 HNMR(400MHz, CDCl 3 )δ7.32-7.27 (m, 2H), 7.24-7.20 (m, 3H), 3.48 (s, 3H), 3.14 (s, 3H), 3.13-3.09 (m, 2H), 3.09-3.03 (m, 2H); 13 CNMR(100MHz, CDCl 3 )δ203.1,140.6,128.5,128.4,126.4,44.9,44.6,41.5,35.7; IR(film)3025,2963,1514,1496,1393,1260,1093,1017,798,700cm -1 ; MS(...

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Abstract

The invention discloses a compounding method for a thioamide compound shown as formula (II). The compounding method comprises the following steps: by taking aldehyde and formyl aliphatic amine as reacting raw materials and taking Na2S.9H2O as a sulfuration reagent, reacting in a water phase under an effect of an oxidizing agent, thereby acquiring the thioamide compound. The compounding method provided by the invention has the advantages that the raw materials are low in cost and are easily acquired, the solvents are green and environment-friendly, the reaction operation is simple, the condition is mild, the substrate is wide in universality, the yield is higher, the functional group tolerance is excellent, the thioamide modification for natural aldehyde and biological active molecule is successively realized, and a method for efficiently constructing the thioamide compound is supplied to the medicinal chemical and biologic orthogonal chemical research.

Description

technical field [0001] The invention belongs to the technical field of synthesis and application of organic compounds, and specifically relates to thioamide compounds and their synthesis methods. Background technique [0002] Thioamide compounds are a very important class of compounds, which are widely used as various drugs and biologically active molecules, as shown in formulas (i) to (iii). Therefore, it is particularly important to construct thioamide compounds starting from some compounds with simple structures and commercially available in large quantities. [0003] [0004] Drug molecules containing thioamide structure [0005] The traditional method of synthesizing thioamides is mainly through amides and Lawson's reagent or phosphorus pentasulfide. In this type of method, the Lawson's reagent used is unstable, relatively expensive, low in atom economy, and has a large odor, and has various degrees of damage to the environment and the human body. The required amid...

Claims

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Application Information

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IPC IPC(8): C07D295/194C07C327/44C07C327/46C07C327/48C07D333/38C07D213/83C07D307/85C07J43/00
CPCC07C327/44C07C327/46C07C327/48C07D213/83C07D295/194C07D307/85C07D333/38C07J9/00C07J43/00
Inventor 姜雪峰魏建朋李一鸣
Owner EAST CHINA NORMAL UNIVERSITY
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