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Method for coupling nitroaromatic compound and boric acid compound to synthesize sulfonamide compound

A technology of boronic acid compounds and nitroaromatic hydrocarbons, applied in the preparation of sulfonic acid amides, the formation/introduction of sulfonyl/sulfinyl groups, organic chemistry, etc., can solve the lack of universality, sulfonyl chloride or sodium aryl sulfinate There are few types, difficult preparation and other problems, to achieve the effect of low price, wide substrate applicability and high reaction yield

Active Publication Date: 2019-10-25
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, iron-catalyzed sulfonyl chloride or sodium arylsulfinate is used in the above reaction to carry out reductive coupling with nitroaromatics to prepare sulfonamide. On the one hand, metal residues are a problem that cannot be ignored in the field of medicine. There are few types of sodium sulfinate, the preparation is difficult, and the lack of universality

Method used

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  • Method for coupling nitroaromatic compound and boric acid compound to synthesize sulfonamide compound
  • Method for coupling nitroaromatic compound and boric acid compound to synthesize sulfonamide compound
  • Method for coupling nitroaromatic compound and boric acid compound to synthesize sulfonamide compound

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Experimental program
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Effect test

Embodiment 1

[0033]

[0034] To the dry sealed tube, add 74 mg of the above nitroaromatics, 88 mg of phenylboronic acid, 267 mg of K 2 S 2 o 5 , 160mg of tripotassium phosphate trihydrate, 32mg of 18-crown-6 and 1.8mL of acetonitrile, then tighten the screw cap of the sealing tube, and react at 100°C for 12h. After the reaction was completed, it was filtered with diatomaceous earth, concentrated, and passed through a silica gel column to obtain 110 mg of the product with a yield of 79%.

[0035] Carry out nuclear magnetic resonance analysis to the product that present embodiment prepares:

[0036] 1 H NMR (400MHz, CDCl 3 )δ7.83(d, J=7.3Hz, 2H), 7.53-7.50(m, 2H), 7.42(t, J=7.7Hz, 2H), 7.22(t, J=7.8Hz, 2H), 7.13- 7.07(m,3H); 13 C NMR (100MHz, CDCl 3 ) δ 138.9, 136.5, 133.1, 129.3, 129.1, 127.3, 125.4, 121.6.

Embodiment 2

[0038]

[0039] Add 82 mg of the above nitroaromatics, 146 mg of phenylboronic acid, 456 mg of Na 2 S 2 o 5 , 255mg of tripotassium phosphate, 334mg of tetrabutylammonium chloride and 3.6mL of dimethyl sulfoxide, and then tighten the screw cap of the sealing tube, and react at 130°C for 36h. After the reaction was completed, it was filtered with diatomaceous earth, concentrated, and passed through a silica gel column to obtain 89 mg of the product with a yield of 60%.

[0040] Carry out nuclear magnetic resonance analysis to the product that present embodiment prepares:

[0041] 1 H NMR (400MHz, CDCl 3 )δ7.79(d, J=7.2Hz, 2H), 7.52(t, J=7.4Hz, 1H), 7.42(t, J=7.6Hz, 2H), 7.18(br, 1H), 7.03-6.96( m,4H),2.26(s,3H); 13 C NMR (100MHz, CDCl 3 ) δ 139.0, 135.5, 133.7, 132.9, 129.9, 129.0, 127.3, 122.4, 20.9.

Embodiment 3

[0043]

[0044] Add 92 mg of the above nitroaromatics, 146 mg of phenylboronic acid, 460 mg of K 2 S 2 o 5 , 166mg of potassium carbonate, 213mg of tetrabutylammonium bromide and 3mL of acetonitrile, then tighten the screw cap of the sealing tube, and react at 130°C for 24h. After the reaction was completed, it was filtered with diatomaceous earth, concentrated, and passed through a silica gel column to obtain 115 mg of the product with a yield of 73%.

[0045]Carry out nuclear magnetic resonance analysis to the product that present embodiment prepares:

[0046] 1 H NMR (400MHz, CDCl 3 )δ7.72(d, J=7.3Hz, 2H), 7.53(t, J=7.4Hz, 1H), 7.42(t, J=7.7Hz, 2H), 6.98(d, J=8.9Hz, 2H) ,6.82(br,1H),6.75(d,J=8.9Hz,2H),3.74(s,3H); 13 CNMR (100MHz, CDCl 3 ) δ 158.1, 138.9, 132.9, 129.0, 128.6, 127.3, 125.7, 114.5, 55.4.

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Abstract

The invention belongs to the field of organic synthesis, and specifically discloses a method for coupling a nitroaromatic compound and a boric acid compound to synthesize a sulfonamide compound. The method for coupling the nitroaromatic compound and the boric acid compound to synthesize the sulfonamide compound comprises the steps that in an organic solvent, pyrosulfite is used as a source of SO2,and heating is carried out for a coupling reaction, and then after the post-treatment, the sulfonamide compound is obtained. The method for coupling the nitroaromatic compound and the boric acid compound to synthesize the sulfonamide compound is simple in operation, does not require nitrogen protection, and can be carried out under air. The nitroaromatic compound and the boric acid compound are abundant in source, relatively low in price, high in reaction yield, wide in applicability of a substrate and free in metal residual. The method for coupling the nitroaromatic compound and the boric acid compound to synthesize the sulfonamide compound can be used for synthesizing a series of sulfonamide compounds, and the synthesized compounds have wide application value in the fields of pesticidesand medicines.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a method for synthesizing sulfonamide compounds by coupling nitroaromatics and boric acid compounds. Background technique [0002] Sulfonamide compounds have been widely used in pesticides, medicine and other fields (Scott, K.A.; Njardarson, J.T. Top. Curr. Chem. (Z) 2018, 376, 376). The traditional method of synthesizing sulfonamides often uses sulfonyl chloride and amine to react under the action of alkali. Although this method is efficient, it is difficult to prepare sulfonyl chloride, has poor functional group compatibility, is sensitive to water, and is difficult to preserve. It is easy to develop a new It is of great significance to replace the traditional method of synthesizing sulfonamides with efficient coupling mode. [0003] Nitroaromatics are basic chemical industry raw materials with wide sources and cheap prices, and most of the traditional raw material amines for ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07B45/04C07C303/36C07D209/08C07D213/71C07D215/38C07D261/10C07D295/135C07D307/85C07D333/34C07D333/62C07C311/21C07C311/29C07C311/08
CPCC07B45/04C07C303/36C07D209/08C07D213/71C07D215/38C07D261/10C07D295/135C07D307/85C07D333/34C07D333/62C07C311/21C07C311/29C07C311/08
Inventor 陈万芝陈凯
Owner ZHEJIANG UNIV
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