Unlock instant, AI-driven research and patent intelligence for your innovation.
Reduction method of benzoaromatic nitrogen heterocyclic compounds
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 nitrogen heterocycle and compound technology, applied in the field of organic synthesis, can solve the problems of long reaction route, complicated operation, and existence of danger
Active Publication Date: 2019-11-08
CHINA THREE GORGES UNIV
View PDF1 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
[0004] In the above synthetic method, the hydrogenation reaction uses hydrogen as the hydrogen source of the reaction, which is inconvenient and dangerous to operate, and the scope of application of the substrate is limited; the Diels-Alder reaction requires a conjugated double bondsystem in the structure of the substrate, and the substrate The adaptability is not extensive; the reaction route of the multi-step reaction is long, the time is long, the operation is complicated, and the total yield is low; the raw material structure used in the multi-component reaction and the domino reaction is particularly complicated and difficult to prepare, which is not suitable for industrial production. Therefore, the research on the synthetic method of tetrahydroquinoline compounds is of great significance
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
[0036] Synthesis of 2-Methyltetrahydroquinoline
[0037]
[0038] 2-Methylquinoline (0.3mmol, 43mg), Tetrahydroxydiboron (0.9mmol, 81mg), Pd(OAc) 2 (0.015mmol, 3.5mg) was added in 1mL acetonitrile, reacted for 12 hours at 40°C, purified by thin-layer chromatography to obtain 12mg of 2-methyltetrahydroquinoline, the yield was 27%, and the purity was 98%. 1 H NMR (400MHz, CDCl 3 ):δ=1.28(d,3H,CH 3 ),1.68(m,1H),2.01(m,1H),2.77-2.95(m,2H),3.47(m,1H),3.67(br,1H),6.54(d,1H),6.70(t, 1H),7.05(t,2H)ppm; 13 C NMR (100MHz, CDCl 3 ): δ=22.75, 26.74, 47.26, 114.15, 117.08, 121.20, 126.82, 129.40, 144.91ppm.
Embodiment 2
[0040] Synthesis of 2-Methyltetrahydroquinoline
[0041]
[0042] 2-Methylquinoline (0.3mmol, 43mg), Tetrahydroxydiboron (0.9mmol, 81mg), Cu(OAc) 2 (0.015mmol, 2.5mg) was added into 1mL of acetonitrile, reacted at 40°C for 12 hours, and purified by thin layerchromatography to obtain 42.8mg of 2-methyltetrahydroquinoline with a yield of 97% and a purity of 98%.
Embodiment 3
[0044] Synthesis of 2-Methyltetrahydroquinoline
[0045]
[0046] 2-Methylquinoline (0.3mmol, 43mg), tetrahydroxydiboron (0.9mmol, 81mg), and CuI (0.015mmol, 5mg) were added to 1mL acetonitrile, reacted at 40°C for 12 hours, and purified by thin layerchromatography to obtain 2 -Methyltetrahydroquinoline 29.6 mg, the yield was 67%, and the purity was 98%.
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 method for reducing benzo aromanitrogen-heterocycle. According to the method, the benzo aromanitrogen-heterocycle is taken as a raw material, dual-boric acid is taken as a hydrogen source, lewis acid is taken as a catalyst, acetonitrile is taken as a solvent and the benzo aromanitrogen-heterocyclic compound is acquired under suitable temperature and at suitable time. The method for reducing the benzo aroma nitrogen-heterocyclic compound, provided by the invention, has the advantages of mild condition, low cost, high yield, simplicity in post-processing and suitability for industrial production. The process route is as follows.
Description
technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a method for reducing benzoaromatic nitrogen heterocyclic compounds. Background technique [0002] Benzoazepine heterocyclic compounds have a variety of pharmacological activities, and have shown good activities in anticancer, antifungal and analgesic aspects. In addition, it can also be used to prevent and treat arteriosclerosis, hyperlipidemia and dyslipidemia. At the same time, benzazepine heterocyclic compounds are also used in the treatment of renal failure, coronary heart disease, and Cushing's syndrome. In addition, benzazine heterocyclic compounds are also chromophores with good electron donating ability, and the disperse dyes used as electron donating bodies have the advantages of bright shade, deep color effect and extinction coefficient. [0003] Due to the special use of this type of compound, in recent years, a large number of synthetic method...
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