1, 2, 3-triazole-2-oxide and preparation method thereof
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 oxides and compounds, which is applied in the field of 1,2,3-triazole-2-oxide and its preparation, can solve the problems of limited substrate range and harsh reaction conditions, and achieve simple operation, easy product, The effect of a wide range of substrates
Active Publication Date: 2021-06-08
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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
The preparation of 1,2,3-triazole derivatives mainly uses transition metals to catalyze the cycloaddition reaction of organic azides and terminal alkynes (J.Am.Chem.Soc.2017,139,12121), this method requires the use of Potentially dangerous azide; In addition, methods without azide participation have also been reported (Angew.Chem.Int.Ed.2013,52,13324; Org.Chem.Front.2018,5,571), but the reaction conditions are harsh, and Substrate range limited
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
[0033]
[0034] In a 25mL sealed tube, add enaminone compound 2a (104mg, 0.5mmol), 4A molecular sieve 100mg, CuCl 2 (7mg, 0.05mmol), add 5mL MeCN, tert-butyl nitrite 3 (180μL, 1.5mmol) in an argon atmosphere, react at 80°C for 3h, and separate directly by column chromatography after the reaction (eluent, petroleum ether (60-90 ℃) / ethyl acetate=2:1, v / v), to obtain a light yellow solid product 1a (83 mg, yield 66%), melting point 82-83 ℃, the target product was determined by NMR and high-resolution mass spectrometry, the result as follows:
[0035] 1 H NMR (400MHz, CDCl 3 )δ8.15(m,2H,aromatic CH),7.57 and 7.46(t each,J=7.4 and 7.7Hz,1:2H,aromatic CH),3.92 and 2.58(s each,3:3H,2×CH 3 ). 13 C{ 1 H}NMR (100MHz, CDCl 3 )δ183.9(Cq,CO),136.6,136.5,and 128.51(Cq),133.5,130.5,and 128.45(aromatic CH),32.0 and 19.1(2×CH 3 ).HRMS(EI)m / z calcd for C 11 h 12 N 3 o 2 S[M+H] + :250.0650; Found: 250.0656.
Embodiment 2
[0037] The difference from Example 1 is that the solvent is dichloromethane to obtain the target product 1a (35 mg, yield 28%).
Embodiment 3
[0039] The difference from Example 1 is that the solvent is toluene, and the target product 1a (50 mg, yield 40%) is obtained.
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
Property
Measurement
Unit
melting point
aaaaa
aaaaa
Login to view more
Abstract
The invention relates to 1, 2, 3-triazole-2-oxide and a preparation method thereof, and belongs to the technical field of chemical organic synthesis. The structure of the 1, 2, 3-triazole-2-oxide is as shown in formula 1 in the specification, wherein, R1 is C1-4 alkyl, aryl or aryl vinyl, the aryl of R1 is phenyl, aryl with a substituent group on a benzene ring or heterocyclic aryl, R2 is C1-4 alkyl or benzyl, R3 is C1-4 alkyl or aryl, and the aryl of R3 is phenyl, aryl with a substituent group on a benzene ring or heterocyclic aryl. The 1, 2, 3-triazole-2-oxide with various structures is obtained from simple and easily available raw materials, an azide is not required to be used in the reaction, the operation is simple and convenient, the substrate application range is wide, and the product is easy to convert.
Description
technical field [0001] The invention relates to a 1,2,3-triazole-2-oxide and a preparation method thereof, belonging to the technical field of chemical organic synthesis. Background technique [0002] Triazole derivatives are very important nitrogen-containing heterocyclic compounds, and are also important structural units of many drug molecules and organic functional materials. They have extremely important application values in various fields such as pharmaceutical science, material science, coordination chemistry, and organic chemistry. . Among them, 1,2,3-triazole derivatives are used in anti-cancer, anti-fungal, anti-epileptic, anti-viral and other drugs due to their unique structure and wide range of biological activities, so about 1,2,3-triazole The research on the synthesis method of derivatives has important scientific significance. The preparation of 1,2,3-triazole derivatives mainly uses transition metals to catalyze the cycloaddition reaction of organic azide...
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
Patent Type & Authority Applications(China)
IPC IPC(8): C07D249/04C07D249/06
CPCC07D249/04C07D249/06
Inventor 吴苹余正坤周永贵
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
Login to view more