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A kind of sulfonyl hydrazone derivative and its preparation method and application

A technology of derivatives and sulfonyl hydrazones, applied in the field of sulfonyl hydrazone derivatives and their preparation, can solve the problems of high yield and no target product, and achieve the effects of reducing pollution and eliminating pollution

Active Publication Date: 2022-06-21
SHAOXING UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

And, when R 3 Substituents with electron-donating groups on the aromatic ring have a higher yield than those connected with electron-deficient groups, and when R 3 When it is an aliphatic group, no corresponding target product is generated

Method used

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  • A kind of sulfonyl hydrazone derivative and its preparation method and application
  • A kind of sulfonyl hydrazone derivative and its preparation method and application
  • A kind of sulfonyl hydrazone derivative and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1～11

[0042] The solvent of embodiment 1~11 adopts CH 3 CN was reacted with different catalysts, and the reaction results are shown in Table 1.

[0043] Table 1 Reaction conditions and results of Examples 1-11

[0044]

[0045]

Embodiment 12～17

[0047] In Examples 12-17, no catalyst was added, and the reaction solvent was changed. The results of the reaction at 60° C. are shown in Table 2.

[0048] Table 2 Reaction conditions and results of Examples 12-17

[0049]

[0050] In Examples 18-20, no catalyst was added, water was used as the reaction solvent, and the results of changing the reaction temperature were shown in Table 3.

[0051] Table 2 Reaction conditions and results of Examples 18-20

[0052]

Embodiment 21～41

[0054] In Examples 21 to 41, no catalyst was added, water was the reaction solvent, the reaction temperature was 60° C., and the substrate was changed. The results obtained are shown in Table 3.

[0055] Table 3 Reaction conditions and results of Examples 21 to 41

[0056]

[0057]

[0058] The structural characterization data of some products are as follows:

[0059]

[0060] Compound (I-1): acetophenone benzenesulfonyl hydrazone: White solid, m.p: 84.5℃-85.5℃. 1 H NMR (400MHz, DMSO-d 6 )δ10.55(s,1H),7.94-7.93(m,1H),7.93-7.92(m,1H),7.68-7.63(m,2H),7.62-7.60(m,3H),7.37-7.36( m, 3H), 2.18(s, 3H); 13 C NMR (101MHz, DMSO-d 6 )δ153.93,139.50,137.79,133.45,129.89,129.51,128.83,127.99,126.42,14.79.HRMS(ESI)M / Zcalcd for C 14 H 15 N 2 O 2 S.[M+H] + :275.0849.Found:275.0855.

[0061]

[0062] Compound (I-2): acetophenone p-toluenesulfonyl hydrazone: White solid, m.p: 320.5℃-321.5℃. 1 H NMR (400MHz, DMSO-d 6 )δ10.52(s,1H),7.82(d,J=8.2Hz,2H),7.63-7.61(m,2H),7.41(d...

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Abstract

The invention discloses a sulfonyl hydrazone derivative and its preparation method and application. The preparation method comprises the following steps: using olefin azide and sulfonyl hydrazide as starting materials, the reaction temperature is 60°C, and the reaction time is 2-4 hours , the reaction solvent is water, no catalyst is added, and the feed ratio of raw materials is olefin azide: sulfonyl hydrazide = 1:1. The reaction reagent used in the present invention is stable, cheap and easy to obtain, and is convenient for large-scale production; in addition, because the reaction does not need to add a catalyst, and water is used as the reaction solvent, the method is safe and economical, and the pollution to the environment is reduced and eliminated from the source. It will not cause damage to the environment and meets the requirements of green chemistry. In addition, the biological activity test results show that the product has certain acetylcholinesterase inhibitory activity, therefore, the preparation method and its product have important application significance in the field of medicine.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a sulfonyl hydrazone derivative and a preparation method and application thereof. Background technique [0002] Sulfonyl hydrazones contain the substructure (-SO 2 NHN=C-), is a special class of Schiff bases. Studies have shown that sulfonyl hydrazones exhibit a wide range of physiological activities, such as antioxidant, anti-inflammatory, antibacterial, insecticidal, antiviral and antitumor. In addition, it also has unique good coordination ability and abundant coordination forms, which can produce many metal coordination compounds with high biological activity, and metal coordination compounds are used in the field of biomedicine such as anticancer drugs. , Magnetic resonance imaging contrast agent research has a very unique position. Due to the special imine structure (-NHN=C-) in the molecular structure of these compounds, they can participate in various chemi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C311/49C07D333/34A61P25/28A61K31/18A61K31/381C07C303/40
CPCC07C311/49C07D333/34A61P25/28
Inventor 王海张耀红
Owner SHAOXING UNIVERSITY
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