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Sulfonamide compound and synthesis method and application thereof

A synthetic method and technology of sulfonamides, applied in the field of organic compound synthesis and application

Inactive Publication Date: 2019-03-08
EAST CHINA NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

On the other hand, although three-component couplings of aryl halides or aryl boronic acids, sulfur dioxide surrogates and alkylamines, hydrazines have been reported, these methods are for the synthesis of secondary and tertiary amines
So far, there is no one-step method to construct a first-order sulfonamide

Method used

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  • Sulfonamide compound and synthesis method and application thereof
  • Sulfonamide compound and synthesis method and application thereof
  • Sulfonamide compound and synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Synthesis of Compound 2a:

[0044]

[0045] Under nitrogen protection, the diazonium salt 1a (257.4mg, 1,25mmol), NaN 3 (32.5mg, 0.5mmol), PPh 3 (157.4mg, 0.6mmol), Na 2 S 2 o 5 (190.1mg, 1.0mmol), TBAB (241.7mg, 0.75mmol) and MeCN / H 2 O=2 / 1 (1 mL) was added to the Schlenk reaction tube. After the reaction was stirred at 80°C for 12 hours, it was lowered to room temperature, and 10 mL of water was added to the system for dilution, then ethyl acetate (10 mL*3) was added for extraction, dried over anhydrous sodium sulfate, filtered, concentrated, and separated by column chromatography to obtain a white solid 2a (90%). 1 H NMR (400MHz, d 6 -DMSO) δ7.71(d, J=8.2Hz, 2H), 7.36(d, J=8.1Hz, 2H), 7.27(s, 2H), 2.37(s, 3H); 13 C NMR (100MHz, d 6 -DMSO) δ141.8, 141.4, 129.3, 125.6, 20.9; IR (KBr) ν3348, 3270, 1598, 1500, 1309, 1175, 1021, 917, 835, 669cm -1 ; HRMS (EI) for C 7 h 9 NO 2 SCalculated: 171.0354,found: 171.0353.

Embodiment 2

[0047] Synthesis of compound 2b:

[0048]

[0049] Under nitrogen protection, the diazonium salt 1b (239.9mg, 1.25mmol), NaN 3 (32.5mg, 0.5mmol), PPh 3 (157.4mg, 0.6mmol), Na 2 S 2 o 5 (190.1mg, 1.0mmol), TBAB (241.7mg, 0.75mmol) and MeCN / H 2 O=2 / 1 (1 mL) was added to the Schlenk reaction tube. After the reaction was stirred at 80°C for 12 hours, it was lowered to room temperature, and 10 mL of water was added to the system for dilution, then ethyl acetate (10 mL*3) was added for extraction, dried over anhydrous sodium sulfate, filtered, concentrated, and separated by column chromatography to obtain a white solid 2b (14.8 mg, 72%). 1 H NMR (400MHz, d 6 -acetone) δ7.91 (d, J=7.0Hz, 2H), 7.72–7.43 (m, 3H), 6.59 (s, 2H); 13 C NMR (100MHz, d 6 -acetone)δ145.0, 132.8, 129.7, 126.8; IR(KBr)ν3353, 3258, 1448, 1344, 1160, 1091, 756, 688, 537cm -1 ; HRMS (EI) for C 6 h 7 NO 2 S Calculated: 157.0197, Found: 157.0200.

Embodiment 3

[0051] Synthesis of compound 2c:

[0052]

[0053] Under nitrogen protection, the diazonium salt 1c (277.4mg, 1.25mmol), NaN 3 (32.5mg, 0.5mmol), PPh 3 (157.4mg, 0.6mmol), Na 2 S 2 o 5 (190.1mg, 1.0mmol), TBAB (241.7mg, 0.75mmol) and MeCN / H 2 O=2 / 1 (1 mL) was added to the Schlenk reaction tube. After the reaction was stirred at 80°C for 12 hours, it was lowered to room temperature, and 10 mL of water was added to the system for dilution, then ethyl acetate (10 mL*3) was added for extraction, dried over anhydrous sodium sulfate, filtered, concentrated, and separated by column chromatography to obtain a white solid 2c (91%). 1 H NMR (400MHz, d 6 -acetone) δ7.83(d, J=8.9Hz, 2H), 7.06(d, J=8.9Hz, 2H), 6.43(s, 2H), 3.87(s, 3H); 13 C NMR (100MHz, d 6 -acetone)δ163.2,137.0,128.9,114.7,56.0; IR(KBr)ν3348,3270,2980,1598,1500,1309,1157,917,835,669cm -1 ; HRMS (EI) for C 7 h 9 NO 3 SCalculated: 187.0303,found: 187.0306.

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Abstract

The invention discloses a synthesis method of a sulfonamide compound represented in a formula (2). According to the method, diazonium salt is used as a reaction raw material, and under the action of an inorganic nitrogen reagent, an inorganic sulfur dioxide reagent, an additive and a phosphine reagent, the diazonium salt is reacted in a solvent at 60-100 DEG C to obtain various sulfonamide compounds. According to the method inorganic salt is used as a nitrogen atom source and a sulfur dioxide source under a metal-free catalytic condition to construct the sulfonamide compound through one step,thereby avoiding the conventional multi-step synthesis of sulfonamide by condensing unstable acid chloride and amine; and the developed sulfonamide synthesis method can be further applied to the synthesis of the arthritis drug celecoxib and the psychotropic drug sulpiride.

Description

technical field [0001] The invention belongs to the technical field of organic compound synthesis and application, and relates to sulfonamide compounds and their synthesis methods and applications. Background technique [0002] Sulfonamide compounds are a very important class of compounds, especially widely used in drug molecules, such as the arthritis drug celecoxib (Celecoxib) shown in formula (B), the psychotropic drug shown in formula (C) The drug sulpiride and the antineoplastic drug Indisulam represented by the formula (D). Therefore, it is particularly important to develop efficient, environmentally friendly, and step-economic methods for the synthesis of sulfonamides. [0003] [0004] The traditional method of synthesizing sulfonamides is mainly through the coupling of aryl halides and mercaptans (phenols), then through chlorination and oxidation to synthesize sulfonyl chlorides, and finally through coupling with amino compounds. The traditional method is throu...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C311/16C07C303/36C07C311/29C07C323/67C07C319/20C07D231/12C07D207/09
CPCC07C311/16C07C303/36C07C311/29C07C319/20C07C323/67C07D207/09C07D231/12
Inventor 姜雪峰王明范巧玲
Owner EAST CHINA NORMAL UNIV
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