Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Method for synthesizing beta-(N-pyrazolyl) ketone compound through base catalysis

A ketone compound and pyrazole-based technology, which is applied in the field of base-catalyzed synthesis of β-ketone compounds, can solve the problems of poor universality of substrates, harsh reaction conditions, difficult separation, etc. Mild conditions and low dosage

Inactive Publication Date: 2019-11-22
SHANGHAI INST OF TECH
View PDF1 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, there are few reports on the Michael addition reaction of pyrazoles and unsaturated ketones, and most of them use transition metals and ionic liquid catalysts. The reaction conditions are harsh, the substrate universality is not wide, the yield is not high and the separation is difficult. difficulty

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
  • Method for synthesizing beta-(N-pyrazolyl) ketone compound through base catalysis
  • Method for synthesizing beta-(N-pyrazolyl) ketone compound through base catalysis
  • Method for synthesizing beta-(N-pyrazolyl) ketone compound through base catalysis

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026]

[0027] Add pyrazole (1.0mmol) and α,β-unsaturated ketone in turn to the reaction tube (1.0mmol), sodium tert-butoxide (0.02mmol), then add solvent toluene 2mL, react at room temperature for 6 hours, concentrate the reaction solution after the reaction, and separate by column chromatography to obtain the corresponding product with an isolated yield of 89%. 1 H NMR (400MHz, CDCl 3 )δ: 3.56(dd, J=5.2, 17.6Hz, 1H), 4.42(dd, J=8.4, 17.6Hz, 1H), 6.04(dd, J=5.2, 8.4Hz, 1H), 6.15(t, J =2.0Hz,1H),7.17~7.37(m,5H),7.41~7.42(m,2H),7.43~7.49(m,3H),7.89(d,J=7.2Hz,2H); HRMS(ESI) :calcd for C 18 h 16 N 2 O[M] + 276.1263, found 276.1276.

Embodiment 2

[0029]

[0030] Add pyrazole (1.1mmol) and α,β-unsaturated ketone in turn to the reaction tube (1.0mmol), sodium tert-butoxide (0.02mmol), then add solvent toluene 2mL, react at room temperature for 8 hours, concentrate the reaction solution after the reaction, and separate by column chromatography to obtain the corresponding product with an isolated yield of 92%. 1 H NMR (400MHz, CDCl 3 )δ: 3.64(dd, J=5.6, 17.6Hz, 1H), 4.43(dd, J=6.8, 17.6Hz, 1H), 6.08(dd, J=5.6, 6.8Hz, 1H), 6.23(s, 1H ), 7.28(d, J=1.6Hz, 4H), 7.43~7.55(m, 5H), 7.96(d, J=6.0Hz, 2H); HRMS(ESI):calcd forC 18 h 15 ClN 2 O[M] + 310.0873, found 310.0875.

Embodiment 3

[0032]

[0033] Add pyrazole (1.2mmol) and α,β-unsaturated ketone in sequence in the reaction tube (1.0mmol), potassium tert-butoxide (0.02mmol), then add 2mL of tetrahydrofuran as a solvent, and react at room temperature for 12 hours. After the reaction, the reaction solution is concentrated and separated by column chromatography to obtain the corresponding product with an isolated yield of 95%. 1 H NMR (400MHz, CDCl 3 )δ: 3.64(dd, J=2.8, 18.0Hz, 1H), 4.43(dd, J=8.0, 18.0Hz, 1H), 6.03~6.11(m, 1H), 6.22(d, J=9.2Hz, 1H ), 7.22(d, J=7.6Hz, 2H), 7.43~7.55(m, 7H), 7.96(d, J=7.2Hz, 2H); HRMS(ESI): calcd for C 18 h 15 BrN 2 O[M] + 354.0368, found 354.0369.

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 a method for synthesizing a beta-(N-pyrazolyl) ketone compound by base catalysis, which comprises the following steps of dissolving pyrazole and alpha, beta-unsaturated ketonein an organic solvent, adding base, reacting at a room temperature for 6-12 hours, and separating and purifying to obtain the beta-(N-pyrazolyl) ketone compound. Compared with the prior art, the method has the advantages of simple and green synthesis process, excellent selectivity, higher yield and wide substrate range, and has the wide application value in the fields of biology, pharmaceutical chemistry industry and the like.

Description

technical field [0001] The invention belongs to the technical field of synthetic chemistry and relates to a method for base-catalyzed synthesis of β-(N-pyrazolyl) ketone compounds. Background technique [0002] The Michael addition reaction of nitrogen-containing compounds and unsaturated ketones (Michael addition reaction) is one of the atom-economical reactions and the most effective ways to form new C-N bonds and synthesize β-aminocarbonyl compounds. The product β-aminocarbonyl compounds It is an important organic synthesis intermediate, which can further synthesize active molecules such as β-amino acid, β-lactam, natural products and drugs. Therefore, it is of great significance to develop an efficient catalytic system for the synthesis of β-ketoesters. [0003] Most pyrazole compounds have important biological activities. In addition to being widely used as herbicides, insecticides, and antifungal agents in the field of pesticides, they have anticancer, antibacterial, ...

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
Patent Type & Authority Applications(China)
IPC IPC(8): C07D231/12
CPCC07D231/12
Inventor 姚子健高永红
Owner SHANGHAI INST OF TECH
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

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

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com