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A method for efficiently preparing nh-1,2,3 triazole compounds

A triazole compound and compound technology, applied in the field of efficient preparation of NH-1,2,3 triazole compounds, to achieve the effect of realizing application value and direct and simple synthesis

Active Publication Date: 2019-03-01
JIANGXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So for electroneutral or electron-rich alkynes, there is no suitable method to prepare NH-1,2,3-triazoles, especially 4,5-disubstituted-NH-1,2,3 -The synthesis of triazoles is still a great challenge to organic synthesis

Method used

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  • A method for efficiently preparing nh-1,2,3 triazole compounds
  • A method for efficiently preparing nh-1,2,3 triazole compounds
  • A method for efficiently preparing nh-1,2,3 triazole compounds

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0021]

[0022] In a clean 25 mL Schlenk tube, add 1,2-diphenylacetylene (0.20 mmol), NaN 3 (0.3mmol), PhI(OAc) 2 (0.2mmol), add 3mL CH 3 CN was used as a solvent, reacted at room temperature for 8 hours, and was detected by TLC spotting. 2 SO 4 After drying, the organic layer was concentrated and subjected to column chromatography to obtain pure 4,5-diphenyl-2H-1,2,3-triazole as a light yellow solid with a yield of 95%.

[0023] 1 H NMR (400MHz, CDCl 3 )δ7.64-7.48(m,4H),7.40-7.27(m,6H).

[0024] 13 C NMR (100MHz, CDCl 3 )δ142.1, 129.9, 128.6, 128.5, 128.2ppm.

[0025] HRMS (ESI) calcd for C 14 h 12 N 3 (M+H) + :222.1031, found 222.1028.

example 2

[0027]

[0028] Into a clean 25 mL Schlenk tube was added 1-methyl-4-(phenylethynyl)benzene (0.20 mmol), NaN 3 (0.3mmol), PhI(OAc) 2 (0.2mmol), add 3mL CH 3 CN was used as a solvent, reacted at room temperature for 8 hours, and was detected by TLC spotting. 2 SO 4 After drying, the organic layer was concentrated and subjected to column chromatography to obtain pure 4-phenyl-5-(p-tolyl)-2H-1,2,3-triazole as a light yellow solid with a yield of 92%.

[0029] 1 H NMR (400MHz, CDCl 3)δ7.71–7.52(m,2H),7.44(d,J=8.0Hz,2H),7.41–7.31(m,3H),7.18(d,J=7.8Hz,2H),2.38(s,3H ).

[0030] 13 C NMR (100MHz, CDCl 3 )δ142.1, 141.9, 138.5, 130.2, 129.3, 128.6, 128.4, 128.2, 128.1, 126.9, 21.3ppm.

[0031] HRMS (ESI) calcd for C 15 h 14 N 3 (M+H) + :236.1188, found 236.1182.

example 3

[0033]

[0034] Into a clean 25 mL Schlenk tube was added 1-methoxy-4-(phenylethynyl)benzene (0.20 mmol), NaN 3 (0.3mmol), PhI(OAc) 2 (0.2mmol), add 3mL CH 3 CN was used as a solvent, reacted at room temperature for 8 hours, and was detected by TLC spotting. 2 SO 4 After drying, the organic layer was concentrated and subjected to column chromatography to obtain pure 4-(4-methoxyphenyl)-5-phenyl-2H-1,2,3-triazole, light yellow solid, yield 79% .

[0035] 1 H NMR (400MHz, CDCl 3 )δ7.60-7.53(m,2H),7.47(d,J=8.6Hz,2H),7.40-7.31(m,3H),6.89(d,J=8.7Hz,2H),3.83(s,3H ).

[0036] 13 C NMR (100MHz, CDCl 3 )δ159.8, 142.1, 141.8, 130.3, 129.5, 128.6, 128.4, 128.1, 122.2, 114.1, 55.2ppm.

[0037] HRMS (ESI) calcd for C 15 h 14 N 3 O(M+H) + :252.1137, found 252.1130.

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Abstract

The invention discloses a method for efficiently preparing NH-1,2,3 triazole compounds, using alkyne compounds to form NaN 3 or TMSN 3 is a nitrogen source, and the oxidizing agent is Ph(OAc) 2 , KMnO 4 , MnO 2 , PhI(CF 3 CO 2 ) 2 , Mn(OAc) 3 , PhIO, (NH 4 ) 2 Ce(NO 3 ) 6 One of them reacts at room temperature to obtain NH-1,2,3 triazole derivatives. The present invention realizes the synthesis of NH-1,2,3-triazoles from simple alkynes, especially electroneutral or rich Electronic alkynes, so that the synthesis of NH-1,2,3-triazole compounds is more direct and concise, and its potential application value can be better realized.

Description

technical field [0001] The invention relates to the field of organic chemistry, in particular to a method for efficiently preparing NH-1,2,3 triazole compounds. Background technique [0002] NH-1,2,3-triazole compounds are a class of five-membered triazine aromatic heterocyclic compounds with extremely important physiological activities, and have a wide range of applications. It not only has good pharmacological activity, but also is a very valuable pharmaceutical intermediate and organic synthesis intermediate, which has been widely used in the fields of medicine, biochemistry, optical materials, material chemistry and emerging chemical biology. Since its discovery, its research in the field of medicine has been particularly active. As a result, chemists have done a lot of research on the drug activity and synthetic routes of this kind of compounds and made amazing progress. For example, in medicine, NH-1,2,3-triazole compounds commonly exist in drug molecules and have bee...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D249/06C07D409/04C07F7/08
CPCC07D249/06C07D409/04C07F7/0814
Inventor 赵军锋胡隆
Owner JIANGXI NORMAL UNIV
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