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1, 2, 3-triazole-2-oxide and preparation method thereof

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
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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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

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  • 1, 2, 3-triazole-2-oxide and preparation method thereof
  • 1, 2, 3-triazole-2-oxide and preparation method thereof
  • 1, 2, 3-triazole-2-oxide and preparation method thereof

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Experimental program
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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.

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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

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Application Information

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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
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