Supercharge Your Innovation With Domain-Expert AI Agents!

N<2> selective enol ether substituted triazole derivatives and preparation method thereof

A technology for triazole and derivatives, which is applied in the field of triazole derivatives and their preparation, can solve the problems of low yield and low selectivity, and achieve the effects of high selectivity, readily available raw materials, and simple operation

Inactive Publication Date: 2016-10-12
SHANGHAI UNIV
View PDF2 Cites 2 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] At present, the synthesis of alkylene etherified triazoles is mainly catalyzed by Lewis acid. The yield of this method is low, and the selectivity is not high, and the products are mostly N 1 , N 2 mixture

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
  • N&lt;2&gt; selective enol ether substituted triazole derivatives and preparation method thereof
  • N&lt;2&gt; selective enol ether substituted triazole derivatives and preparation method thereof
  • N&lt;2&gt; selective enol ether substituted triazole derivatives and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] The following steps are used to prepare 4-phenyl-2-(tetrahydro-2H-pyran-2-yl) 2H-1,2,3-triazole compound: under air atmosphere, add Tetrahydropyran (37.8mg, 0.45mmol), 4-phenyl-1H-1,2,3-triazole (43.5mg, 0.3mmol), iron nitrate nonahydrate (7.3mg, 0.03mmol), 10mL Ethyl chloride, stirred at 60 degrees Celsius for 10 hours, cooled to room temperature after the reaction, filtered with diatomaceous earth, extracted with water and ethyl acetate to remove the solvent, concentrated the organic layer and separated by silica gel column chromatography to obtain 55.0 mg of light yellow oily liquid , the yield was 80%. The structure of this compound is:

[0023]

[0024] Proton NMR spectrum (500MHz, CDCl 3 ): δ=7.94(s,1H),7.84–7.86(m2H),7.43–7.46(m2H),7.36–7.39(m 1H),5.78(dd,J=9.0,2.5Hz,1H),4.09–4.12 (m,1H), 3.77–3.81(m,1H), 2.50–2.53(m,1H), 2.12–2.19(m,2H), 1.66–1.80(m,3H).

[0025] C NMR spectrum (125MHz, CDCl 3 ): δ=148.08, 131.50, 130.08, 128.72, 128.50, 126.03, 89.04, 6...

Embodiment 2

[0029] Preparation of 4-methylphenyl-2-(tetrahydro-2H-pyran-2-yl) 2H-1,2,3-triazole compound adopts the following steps: Add tetrahydropyran (37.8mg, 0.45mmol), 4-methylphenyl-1H-1,2,3-triazole (47.7mg, 0.3mmol), iron nitrate nonahydrate (7.3mg, 0.03mmol) ), 10mL dichloroethane, stirred at 60 degrees Celsius for 10 hours, cooled to room temperature after the reaction, filtered with diatomaceous earth, extracted with water and ethyl acetate to remove the solvent, concentrated the organic layer and separated by silica gel column chromatography to obtain light yellow Oily liquid 56.1 mg, yield 77%. The structure of this compound is:

[0030]

[0031] Proton NMR spectrum (500MHz, CDCl 3 ): δ=7.88(s,1H),7.71(d,J=8.0Hz,2H),7.22(d,J=8.0Hz,2H),5.73(dd,J=9.0,2.5Hz,1H),4.05 –4.08(m,1H),3.73–3.78(m,1H),2.45–2.49(m,1H),2.37(s,3H),2.08–2.15(m,2H),1.62–1.75(m,3H) .

[0032] Carbon NMR spectrum (125MHz, CDCl 3 ): δ = 148.23, 138.49, 131.43, 129.51, 127.36, 126.03, 89.11, 67.49, 29.4...

Embodiment 3

[0036] Preparation of 4-(4-methoxyphenyl)-2-(tetrahydro-2H-pyran-2-yl) 2H-1,2,3-triazole compound adopts the following steps: under air atmosphere, to Add tetrahydropyran (37.8mg, 0.45mmol), 4-(4-methoxyphenyl)-1H-1,2,3-triazole (52.5mg, 0.3mmol) sequentially into a 50mL reaction flask, Ferric nitrate nonahydrate (7.3mg, 0.03mmol), 10mL dichloroethane, stirred at 60 degrees Celsius for 10 hours, cooled to room temperature after the reaction, filtered with diatomaceous earth, extracted with water and ethyl acetate to remove the solvent, and concentrated the organic layer Separated by silica gel column chromatography, 58.3 mg of light yellow oily liquid was obtained with a yield of 75%. The structure of this compound is:

[0037]

[0038] Proton NMR spectrum (500MHz, CDCl 3): δ=7.86(s,1H),7.74(d,J=8.5Hz,2H),6.97(d,J=8.5Hz,2H),5.75(dd,J=9.0,2.5Hz,1H),4.08 –4.11(m,1H),3.86(s,3H),3.76–3.81(m,1H),2.46–2.54(m,1H),2.10–2.17(m,2H),1.66–1.78(m,3H) .

[0039] C NMR spectrum (125M...

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

No PUM Login to View More

Abstract

The invention relates to N<2> selective enol ether substituted triazole derivatives and a preparation method thereof; the derivatives have the structure formula defined in the specification, wherein R is a group defined in the specification, R' is -H, phenyl, chlorine, bromine, methyl, methoxy or trifluoromethyl, R1 is a group defined in the specification, and R'' is -H, chlorine, bromine, methyl or phenyl; or R1 is a group defined in the specification, and R'' is -H, cyclopentyl or cyclohexyl; R2 is -H or methyl. The invention provides a method for the selective alkyl vinyl ether substituted triazole derivatives. Phenyl triazole and alkyl vinyl ether are subjected to a reaction, and the selective enol ether substituted triazole derivatives are prepared through one step, and have the advantages of high selectivity, easily obtained raw materials, low toxicity, mild reaction conditions, simple operation and the like. The triazole derivatives prepared from the reaction can further undergo a reaction to generate other valuable derivatives.

Description

technical field [0001] The present invention relates to a kind of triazole derivatives and preparation method thereof, especially a kind of N 2 Selective enol ether substituted triazole derivatives and methods for their preparation. Background technique [0002] Nitrogen-substituted triazoles have been widely used in materials, medicine and biological research. Compounds such as nitrogen-substituted triazoles exhibit strong anti-inflammatory and antifungal activities. [0003] [0004] N 1 Substituted triazoles are usually synthesized by reacting some unsubstituted triazoles on nitrogen atoms with electrophiles. Includes alkylation, vinylation, allylation and allenylation of triazoles. However, highly selective N 2 There are not many synthetic methods for substituted triazoles. SNAr and Cu-catalyzed triazole alkylation without high regioselectivity emerges N 1 , N 2 Miscellaneous nitrogen-substituted compounds. Recently S.L.Buchwald reported a highly selective N ...

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
no application Login to View More
IPC IPC(8): C07D405/04C07D249/06
CPCC07D405/04C07D249/06
Inventor 郝健何律蒋海珍万文
Owner SHANGHAI UNIV
Features
  • R&D
  • Intellectual Property
  • Life Sciences
  • Materials
  • Tech Scout
Why Patsnap Eureka
  • Unparalleled Data Quality
  • Higher Quality Content
  • 60% Fewer Hallucinations
Social media
Patsnap Eureka Blog
Learn More

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2025 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com