A kind of sulfonyl hydrazone derivative and its preparation method and application
What is Al technical title?
Al technical title is built by PatSnap Al team. It summarizes the technical point description of the patent document.
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
View PDF3 Cites 0 Cited by
Summary
Abstract
Description
Claims
Application Information
AI Technical Summary
This helps you quickly interpret patents by identifying the three key elements:
Problems solved by technology
Method used
Benefits of technology
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
the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more
Image
Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
Click on the blue label to locate the original text in one second.
Reading with bidirectional positioning of images and text.
Smart Image
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...
the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more
PUM
Login to view more
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
the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more
Application Information
Patent Timeline
Application Date:The date an application was filed.
Publication Date:The date a patent or application was officially published.
First Publication Date:The earliest publication date of a patent with the same application number.
Issue Date:Publication date of the patent grant document.
PCT Entry Date:The Entry date of PCT National Phase.
Estimated Expiry Date:The statutory expiry date of a patent right according to the Patent Law, and it is the longest term of protection that the patent right can achieve without the termination of the patent right due to other reasons(Term extension factor has been taken into account ).
Invalid Date:Actual expiry date is based on effective date or publication date of legal transaction data of invalid patent.
Login to view more 
Login to view more