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A kind of preparation method of n-2-quinolyl aryl sulfonamide compound

A technology of quinolinyl aryl sulfonamide and aryl sulfonamide, which is applied in the field of preparation of N-2-quinolyl aryl sulfonamide compounds, can solve the problem of low atom economy, unfriendly environment, and substrate price Expensive and other issues, to achieve the effect of high atom economy, environmental friendliness, and easy availability of raw materials

Active Publication Date: 2017-04-12
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] The substrates of this method are expensive, pre-prepared, environmentally unfriendly, and have low atom economy

Method used

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  • A kind of preparation method of n-2-quinolyl aryl sulfonamide compound
  • A kind of preparation method of n-2-quinolyl aryl sulfonamide compound
  • A kind of preparation method of n-2-quinolyl aryl sulfonamide compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Example 1: Synthesis of 4-Methyl-N-(quinolin-2-yl)benzenesulfonamide (1a)

[0036]

[0037] Accurately weigh p-toluenesulfonamide (42.8mg, 0.25mmol), quinoline nitrogen oxide (36.3mg, 0.25mmol), iodobenzene acetate (40.1mg, 0.125mmol), triphenylphosphine (32.8mg, 0.125 mmol), and sequentially added to a 25mL Schlenk bottle, added purified acetonitrile (0.50mL), and reacted at 20°C for 8h. After the reaction, the solvent was removed under reduced pressure, and petroleum ether / ethyl acetate was used as the eluent, and silica gel column separation was performed. The yield of 4-Methyl-N-(quinolin-2-yl)benzenesulfonamide was 80%. 1 H NMR (400MHz, CDCl 3 )δ11.86(s,1H),7.90–7.85(m,3H),7.63–7.60(m,2H),7.46(d,J=8.5Hz,1H),7.37–7.34(m,1H),7.26 (d, J=5.8Hz, 2H), 6.95(d, J=9.4Hz, 1H), 2.39(s, 3H); 13 C NMR (101MHz, CDCl 3 )δ154.0, 142.6, 140.5, 139.7, 136.3, 131.5, 129.2, 127.9, 126.1, 124.5, 121.2, 120.9, 117.2, 21.3; IR (KBr) υ (cm -1 )3425,3337,3050,3024,1670,1601,1493,14...

Embodiment 2

[0038] Example 2: Synthesis of 4-Nitro-N-(quinolin-2-yl)benzenesulfonamide (1c)

[0039]

[0040] Accurately weigh 4-nitrobenzenesulfonamide (50.5mg, 0.25mmol), quinoline nitrogen oxide (44.3mg, 0.25mmol), iodobenzene acetate (123.5mg, 0.5mmol), triphenylphosphine (17.9mg, 0.125mmol), and sequentially added to a 25mL Schlenk bottle, added refined toluene (3.0mL), and placed in a 60°C oil bath for 7h. After the reaction, the solvent was removed under reduced pressure, and petroleum ether / ethyl acetate was used as eluent, and silica gel column separation was performed. The yield of 4-Nitro-N-(quinolin-2-yl)benzenesulfonamide was 76%. 1H NMR (400MHz, DMSO) δ13.43 (s, 1H), 8.17 (d, J = 8.3Hz, 2H), 7.87 (d, J = 7.9Hz, 1H), 7.74–7.70 (m, 1H), 7.64 –7.57(m,5H),7.44–7.40(m,1H); 13 C NMR (101MHz, DMSO) δ148.4, 141.8, 131.6, 131.4, 130.9, 130.8, 128.2, 128.1, 127.7, 126.9, 123.9, 123.7, 114.8; IR (KBr) υ (cm -1 )3439,3326,2960,2921,2865,1653,1492,1395,1378,1092,1015,908,837,771,75...

Embodiment 3

[0041] Example 3: Synthesis of 4-Methyl-N-(quinolin-2-yl)benzenesulfonamide (1d)

[0042]

[0043] Accurately weigh p-toluenesulfonamide (42.8mg, 0.25mmol), 4-methylquinoline nitrogen oxide (50.5mg, 0.25mmol), iodobenzene acetate (40.1mg, 0.125mmol), triphenylphosphine ( 32.8mg, 0.125mmol), and sequentially added to a 25mL Schlenk bottle, added acetonitrile (2.50mL) and toluene (2.50mL) mixed solvent, 20 ℃ for 8h. After the reaction, the solvent was removed under reduced pressure, and petroleum ether / ethyl acetate was used as the eluent, and silica gel column separation was performed. The yield of 4-Methyl-N-(quinolin-2-yl)benzenesulfonamide was 80%. White solid (62.4mg, 40% yield), mp 225-227℃. 1 H-NMR (d 6 -DMSO,400MHz):12.90(bs,1H),7.86(d,J=8.0Hz,1H),7.80(d,J=7.5Hz,2H),7.68-7.65(m,1H),7.56(d, J=8.1Hz, 1H), 7.42(s, 1H), 7.38-7.33(m, 3H), 2.57(s, 3H), 2.34(s, 3H); 13 C-NMR (d 6 -DMSO,101MHz):155.0,150.9,142.1,141.5,132.2,129.8,126.6,125.5,124.4,121.6,118.8,118.2,115.4...

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Abstract

The invention belongs to the technical field of fine chemical engineering, and discloses a preparation method of N-2-quinolyl aryl sulfonamide compounds. The preparation method can be used for synthesizing a series of N-2-quinolyl aryl sulfonamide compounds from aryl sulfonamide and derivative of quinoline N-oxide by carrying out a heating reaction in an organic solvent with a trivalent iodine compound serving as an oxidant and triarylphosphine compounds functioning as additives. The invention mainly aims at providing a synthesis method of the N-2-quinolyl aryl sulfonamide compounds. The method is simple and efficient, high in atom economy and environment-friendly; the method has the advantages of being simple in method step, easy in obtaining of raw materials, high in atom economy, environment-friendly and the like. The N-2-quinolyl aryl sulfonamide, as an important skeleton structure, can be widely applied to the medicine synthesis field, and has high use value and social and economic benefits.

Description

technical field [0001] The invention relates to a preparation method of N-2-quinolyl aryl sulfonamide compounds, belonging to the technical field of fine chemicals. Background technique [0002] N-2-quinolylarylsulfonamides are an important class of biologically active molecules, whose skeleton structures frequently appear in drug molecules and are widely used in the field of drug synthesis. About the synthesis of N-2-quinolyl aryl sulfonamides, the following two methods are usually adopted: [0003] (1) Coupling reaction of arylsulfonamide and 2-bromoquinoline [0004] [0005] The substrates of this method are expensive, need to be prepared in advance, are not environmentally friendly, and have low atom economy. [See: Baffoe, Jonathan et al. Org. Lett. 2010, 12, 1532.]. [0006] (2) Sulfonyl chloride and 2-aminoquinoline coupling reaction [0007] [0008] The substrates of this method are expensive, need to be prepared in advance, are not environmentally friendl...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D215/38
CPCC07D215/38
Inventor 于晓强包明冯秀娟章阅郭明菊
Owner DALIAN UNIV OF TECH