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

Preparation method of 3-quinolyl-5-trifluoromethyl substituted 1, 2, 4-triazole compound

A trifluoromethyl and quinoline-based technology, applied in the field of organic synthesis, can solve the problems of not being suitable for large-scale synthesis applications, and achieve the effects of strong designability, wide tolerance range, and strong practicability

Active Publication Date: 2021-08-27
HANGZHOU VOCATIONAL & TECHN COLLEGE
View PDF7 Cites 5 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to some obvious disadvantages, this method is not suitable for large-scale synthetic applications

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
  • Preparation method of 3-quinolyl-5-trifluoromethyl substituted 1, 2, 4-triazole compound
  • Preparation method of 3-quinolyl-5-trifluoromethyl substituted 1, 2, 4-triazole compound
  • Preparation method of 3-quinolyl-5-trifluoromethyl substituted 1, 2, 4-triazole compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1～15

[0039] Add tetrabutylammonium iodide, tert-butanol peroxide aqueous solution, diphenyl phosphoric acid, trifluoroethylimide hydrazide (II), and 2-methylquinone into a 35mL Schlenk tube according to the raw material ratio in Table 1. Phenyl (III) and organic solvent 2mL, mixed and stirred evenly, reacted according to the reaction conditions in Table 2, filtered after the reaction was completed, mixed with silica gel, purified by column chromatography to obtain the corresponding 3-quinolyl-5-trifluoromethyl Substituted 1,2,4-triazole compound (I), the reaction process is shown in the following formula:

[0040]

[0041] The raw material addition of table 1 embodiment 1~15

[0042]

[0043]

[0044] Table 2

[0045]

[0046] In Table 1 and Table 2, T is the reaction temperature, t is the reaction time, Ph is phenyl, Me is methyl, OMe is methoxyl, t-Bu is ethyl, and DMSO is dimethylsulfoxide.

[0047] The structural confirmation data of the compounds prepared in Exam...

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 discloses a preparation method of a 3-quinolyl-5-trifluoromethyl substituted 1, 2, 4-triazole compound, which comprises the following steps: adding tetrabutylammonium iodide, a tert-butyl hydroperoxide aqueous solution, diphenyl phosphoric acid, trifluoroethyl imine hydrazide and 2-methylquinoline into an organic solvent, heating to 80-100 DEG C, reacting for 8-14 hours completely, and performing post-treatment to obtain the 3-quinolyl-5-trifluoromethyl substituted 1, 2, 4-triazole compound. The preparation method is simple to operate, the initial raw materials are cheap and easy to obtain, the reaction does not need to be operated under anhydrous and anaerobic conditions, a heavy metal does not need to be used as a catalyst, and the 1, 2, 4-triazole compound which is diverse in substitution at different positions and simultaneously contains quinolyl and trifluoromethyl can be synthesized through substrate design. And the applicability of the method is widened while the operation is convenient.

Description

technical field [0001] The invention belongs to the field of organic synthesis, in particular to a preparation method of a 3-quinolyl-5-trifluoromethyl-substituted 1,2,4-triazole compound. Background technique [0002] 1,2,4-Triazole compound is an extremely important five-membered nitrogen-containing heterocyclic ring, which widely exists in many molecular skeletons with biological activity (Chem. Rev. 2010, 110, 1809). Many pharmaceutical intermediates and functional material molecules contain 1,2,4-triazole structures. 1,2,4-Triazole molecules can also be used as ligands to coordinate with transition metals, and are often used in organic light-emitting diodes (Coord.Chem.Rev., 2003, 241, 119). Especially when the triazole molecule is connected with other heterocyclic molecules, it is expected to be used as a bidentate ligand for various cross-coupling reactions. [0003] [0004] Nowadays, there are not many synthetic methods for the preparation of quinoline-substitu...

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): C07D401/04
CPCC07D401/04
Inventor 王慧
Owner HANGZHOU VOCATIONAL & TECHN COLLEGE
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