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

Method for preparing 2-amino-4(3H)-quinazolinones

A technology for aminoquinazoline and ketone compounds, which is applied in the field of catalytic preparation of 2-aminoquinazolin-4-one compounds, and can solve the problem of high reaction cost, high process complexity, complex and rare starting materials, and too many reaction steps and other problems, to achieve the effect of simple and controllable preparation process, simple post-treatment and high reactivity

Inactive Publication Date: 2013-12-25
SUZHOU UNIV
View PDF3 Cites 4 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] In addition to these types of methods, there are still some synthetic routes, some of which require complex and rare starting materials, some require high pressure conditions, and the reaction cost and complexity of the process are relatively high.
[0008] Although the synthetic methods currently reported can prepare 2-aminoquinazolin-4-one compounds, they generally have various defects, such as expensive precursors or complicated preparations, too many reaction steps, harsh reaction conditions, etc.; therefore, the development of A green and environmentally friendly approach to the efficient catalytic synthesis of 2-aminoquinazolin-4-one compounds under mild and convenient conditions is necessary
[0009] Another bimetallic cationic complex [Ln(CH 3 EN) 9 ] 3+ [(AlCl 4 ) 3 ] 3– ·CH 3 CN is a kind of homogeneous catalyst, which can catalyze the polymerization and isomerization of olefins and cycloolefins, and its synthesis method has been reported (see: Hu Jingyu; Shen Qi; Jin Zhongsheng. A new type of rare earth acetonitrile cation complex [Ln( CH 3 EN) 9 (AlCl 4 ) 3 ] CH 3 Synthesis of CN. Scientific Bulletin 1989, 34, 1554), but the application of such complexes in the synthesis of 2-aminoquinazolin-4-one compounds has not been reported

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 preparing 2-amino-4(3H)-quinazolinones
  • Method for preparing 2-amino-4(3H)-quinazolinones
  • Method for preparing 2-amino-4(3H)-quinazolinones

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Example 1: Catalyst [La(CH 3 CN) 9 ] 3+ [(AlCl 4 ) 3 ] 3– ·CH 3 Synthesis of CN

[0038] In the reaction flask that has been dehydrated and deoxygenated, the molar ratio is 1:3 under the protection of argon, and weigh 0.61 g (2.5 mmol) of LaCl 3 And 1.00 g (7.5 mmol) anhydrous AlCl 3 , Add 25 mL of acetonitrile to dissolve, stir at room temperature for 24 hours, centrifuge, take the supernatant, concentrate and stand in a refrigerator at 0 ℃, the obtained crystal is [La(CH 3 CN) 9 ] 3+ [(AlCl 4 ) 3 ] 3– ·CH 3 CN, the yield is 40%.

[0039] The product is white, elemental analysis: La, (13.16±0.5)%, Cl, (40.29±0.5)%.

Embodiment 2

[0040] Example 2: Catalyst [Nd(CH 3 CN) 9 ] 3+ [(AlCl 4 ) 3 ] 3– ·CH 3 Synthesis of CN

[0041] Weigh 0.63 g (2.5 mmol) of NdCl in a reaction flask that has been dehydrated and deoxygenated under the protection of argon gas at a molar ratio of 1:3 3 And 1.00 g (7.5 mmol) anhydrous AlCl 3 , Add 25 mL of acetonitrile to dissolve, stir at room temperature for 24 hours, centrifuge, take the supernatant, concentrate and stand in the refrigerator at 0 ℃, the obtained crystal is [Nd (CH 3 CN) 9 ] 3+ [(AlCl 4 ) 3 ] 3– ·CH 3 CN, the yield is 45%.

[0042] The product is lavender. Elemental analysis: Nd, (13.59±0.5)%, Cl, (40.09±0.5)%.

Embodiment 3

[0043] Example 3: Catalyst [Sm(CH 3 CN) 9 ] 3+ [(AlCl 4 ) 3 ] 3– ·CH 3 Synthesis of CN

[0044] Weigh out 0.64 g (2.5 mmol) of SmCl in a reaction flask that has been dehydrated and deoxygenated under the protection of argon gas at a molar ratio of 1:3 3 And 1.00 g (7.5 mmol) anhydrous AlCl 3 , Add 25 mL of acetonitrile to dissolve, stir at room temperature for 24 hours, centrifuge, take the supernatant, concentrate and stand in a refrigerator at 0 ℃, the obtained crystal is [Sm (CH 3 CN) 9 ] 3+ [(AlCl 4 ) 3 ] 3– ·CH 3 CN, the yield was 53%.

[0045] The product is light yellow. Elemental analysis: Sm, (14.10±0.5)%, Cl, (39.90±0.5)%.

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 preparing 2-amino-4(3H)-quinazolinones. Specifically, a bimetallic cationic complex [Ln(CH3CHN)9]<3+>[(AlCl4)3]<3->.CH3CN is taken as a catalyst, a methyl 2-aminobenzoate compound and a carbodiimide compound are catalyzed for preparation of 2-amino-4(3H)-quinazolinones, wherein Ln represents a positive trivalent rare earth metal ion and is one selected from lanthanum, neodymium, samarium, gadolinium, erbium and ytterbium, CH3CN represents acetonitrile, and the chemical structural general formula of methyl 2-aminobenzoates and the general formula of carbodiimides are both shown in the description. The bimetallic cationic catalyst disclosed by the invention has high activity and has universality for multiple methyl 2-aminobenzoates and carbodiimides; the preparation method is short in reaction time, mild in reaction conditions, high in target product yield, and simple and controllable in preparation process, and has industrialization application potential.

Description

Technical field [0001] The invention belongs to the technical field of preparation of organic nitrogen heterocyclic compounds, and specifically relates to a method for the catalytic preparation of 2-aminoquinazolin-4-one compounds. Background technique [0002] Quinazoline structural units are widely present in biologically active natural products and pharmaceutical molecules. Among them, compounds containing 2-aminoquinazolin-4-one skeleton have been confirmed to have a variety of important biological activities, and they have been approved by researchers. attention. [0003] In the prior art, there are mainly three commonly used methods for synthesizing 2-aminoquinazolin-4-one compounds as follows: [0004] First, the 2-aminoquinazolin-4-one compound is obtained by the nucleophilic substitution reaction between the quinazoline parent ring and the amine at the 2-position. For example, J. DeRuiter reacts 2-chloroquinazolin-4-one with aniline or benzylamine for 1 to 5 hours in DMF s...

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): C07D239/95
Inventor 李云辉姚志刚徐凡
Owner SUZHOU UNIV
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