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

Method for selectively synthesizing polysubstituted dihydroquinazolinone or quinazolinone

A technology of dihydroquinazolinone and quinazolinone is applied in chemical instruments and methods, organic compound/hydride/coordination complex catalysts, organic chemistry and other directions, and can solve problems such as poor stability and operability, The problems such as non-recyclable and recycled use, and the catalyst is not easy to recover, to achieve the effect of convenient large-scale production, simple synthesis method and high recovery rate

Active Publication Date: 2019-10-25
CHANGSHU INSTITUTE OF TECHNOLOGY
View PDF3 Cites 3 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

For example, in 2007, Jiuxi Chen et al. reported [Bmim]BF 4 –H 2 The "one-pot method" synthesis of dihydroquinazolinone with O as the reaction medium (Green Chem., 2007, 9, 972–975), but this method requires a large amount of ionic liquid as the reaction solvent, and it cannot be recycled and reused
CN104744380B discloses a high-acidity ionic liquid as a catalyst, a method for synthesizing dihydroquinazolinone with water and ethanol mixed reaction solvent, but this method requires a large amount of reaction solvent, and the catalyst can only be recovered in an aqueous solution state, stability and operability not good
CN106496146A discloses a method of using sulfonic acid ionic liquid as a catalyst to controlly prepare dihydroquinazolone and quinazolinone derivatives through anthranilamide derivatives and aldehydes by regulating the reaction temperature, but This method still needs a reaction solvent, and the catalyst is not easy to recover. In addition, precise temperature control conditions are required, which requires high equipment requirements in industrial production.
So far, there is no report on the application of heteropolyacid ionic liquids to the synthesis of dihydroquinazolones and quinazolinone derivatives

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 selectively synthesizing polysubstituted dihydroquinazolinone or quinazolinone
  • Method for selectively synthesizing polysubstituted dihydroquinazolinone or quinazolinone
  • Method for selectively synthesizing polysubstituted dihydroquinazolinone or quinazolinone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Embodiment 1 uses isatoic anhydride, aniline and benzaldehyde as raw materials to synthesize 2,3-diphenyl-2,3-dihydroquinazolin-4 (1H)-ones using different kinds of heteropolyacid ionic liquids For comparative experiments, the experiments were divided into eight groups, and each group was added with different kinds of heteropolyacid ionic liquids

[0030] Group A: [MIMPS] 3 PMo 12 o 40

[0031] Group B: [MIMPS] 3 PW 12 o 40

[0032] Group C: [PyPS] 3 PMo 12 o 40

[0033] Group D: [PyPS] 3 PW12O 40

[0034] Group E: [TEAPS] 3 PMo 12 o 40

[0035] Group F: [TEAPS] 3 PW 12 o40

[0036] Group G: H 3 PW 12 o 40

[0037] Group H: PyPSCl

[0038] The specific experimental method is as follows:

[0039] (1) 2mmol of isatoic anhydride, 2.5mmol of aniline, 2.5mmol of benzaldehyde and 0.04mmol of the ionic liquid of the A-G group or 0.12mmol of the ionic liquid of the H group are sequentially added to the reactor, stirred and mixed evenly;

[0040] (2) T...

Embodiment 2

[0044] Example 2 Using isatoic anhydride, aniline and benzaldehyde as raw material to synthesize 2,3-diphenyl-2,3-dihydroquinazolin-4(1H)-ketone using different amounts of [PyPS] 3 PW 12 o 40 The comparative experiment, the experiment is divided into six groups, each group added different amounts of [PyPS] 3 PW 12 o 40

[0045] Group A: 1mol%, [PyPS] 3 PW 12 o 40

[0046] Panel B: 2mol%, [PyPS] 3 PW 12 o 40

[0047] Panel C: 3mol%, [PyPS] 3 PW 12 o 40

[0048] Panel D: 4mol%, [PyPS] 3 PW 12 o 40

[0049] Group E: 5mol%, [PyPS] 3 PW 12 o 40

[0050] Group F: 6mol%, [PyPS] 3 PW 12 o 40

[0051] The specific experimental method is as follows:

[0052] (1) Add 2mmol of isatoic anhydride, 2.5mmol of aniline, 2.5mmol of benzaldehyde and the heteropolyacid ionic liquids of A-F groups respectively into the reactor, stir and mix evenly;

[0053] (2) The reactor was heated by microwave heating to 90° C. to start the reaction, and after 0.5 h of reaction, the...

Embodiment 3

[0058] (1) Mix isatoic anhydride 2mmol, aniline 2.5mmol, benzaldehyde 2.5mmol and [PyPS] 3 PW 12 o 40 Add 0.04mmol to the reactor in turn, stir and mix evenly;

[0059] (2) add hydrogen peroxide 3.0mmol;

[0060] (3) The reactor was heated to 90° C. to start the reaction by microwave heating, cooled to room temperature after 1 hour of reaction, and ethyl acetate was added into the reactor, and stirred to dissolve. Suction filtration after standing still, and the filtrate can be further recrystallized through a mixed solvent of ethanol and water or purified by column chromatography after vacuum distillation. 2,3-Diphenylquinazolin-4(1H)-one was obtained in 88% yield. The filter cake is dried to become a heteropolyacid ionic liquid catalyst, which can be recycled and stored, and can also be recycled and reused at least 6 times.

[0061] 2,3-Diphenylquinazolin-4(1H)-one: 2,3-diphenylquinazolin-4(3H)-one

[0062] White soil. Mp: 148.1-150.9℃; 1H NMR (400MHz, CDCl3) δ8.36 (d...

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 method for selectively synthesizing polysubstituted dihydroquinazolinone or quinazolinone. According to the method, heteropolyacid ion liquid is taken as a catalyst, microwave heating and solvent-free synthesis technologies are utilized, and dihydroquinazolinone and quinazolinone derivatives are selectively synthesized through a 'one-pot-method' synthetic strategy with isatoic anhydride or derivatives of the isatoic anhydride, amine and aldehyde as raw materials. Compared with the prior art, the method has the multiple advantages that the efficiency is high, the costis low, environmental friendliness is realized, reaction selectivity is good, the product yield is high, selective synthesis can be realized, the catalyst is convenient to recover and apply, operationis easy, and industrial mass production is convenient, and the method is an environment-friendly efficient selective synthesis novel method and meets the environment-friendly and chemical developmentidea.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis chemistry, and specifically relates to a green and efficient selective synthesis method of multi-substituted dihydroquinazolones or quinazolinones. Background technique [0002] Dihydroquinazolones and quinazolinones are a class of nitrogen-containing heterocyclic compounds with broad-spectrum biopharmaceutical activities, and their derivatives are widely used in many fields such as medicine, pesticides and materials. For example, it has shown good biological activity in sterilization, anti-inflammation, pain relief, anti-hypertensive, anti-diabetic, anti-cancer and other aspects in medical research. Some of these natural alkaloids also contain quinazolinone-like skeletons, such as halosine, which has antimalarial effects. At the same time, dihydroquinazolone and quinazolinone derivatives have insecticidal, herbicidal and antiviral activities, and the herbicide bentazone that has been m...

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): C07D239/91B01J31/02
CPCB01J31/0281B01J31/0284C07D239/91
Inventor 杨洋付任重刘洋蔡静曾小君
Owner CHANGSHU INSTITUTE OF TECHNOLOGY
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