Polysubstituted quinazoline imine derivative and preparation method thereof

A technology for quinazoline imine and derivatives, which is applied in the field of polysubstituted quinazoline imine derivatives and their preparation, can solve the problems of reduced reaction yield, difficulty in preparation, harm and the like, and achieves high yield and synthesis. The method is simple, the synthesis method is scientific and reasonable

Active Publication Date: 2014-11-19
TSINGHUA UNIV
View PDF6 Cites 1 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] Utilize above-mentioned method in laboratory quinazoline imine derivative, have obvious shortcoming: 1) existing method all needs to use the big raw material of toxicity, as nitromethane, isocyanate, phosphorus oxychloride etc., to environment, All cause great harm to the human body; and other raw materials such as 2-(((phenylimino)methylene) amino)benzonitrile, alkenyl isocyanate, pyrrolidine, etc. are difficult to produce except o-aminobenzonitrile. 2) most of the reactions require multi-step synthesis, thereby reducing the yield of the reaction and increasing the difficulty of producing the product; 3) it is difficult to synthesize many substituted quinazoline imine derivatives, especially diaryl quinazoline The synthetic method of imine has not been reported so far

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
  • Polysubstituted quinazoline imine derivative and preparation method thereof
  • Polysubstituted quinazoline imine derivative and preparation method thereof
  • Polysubstituted quinazoline imine derivative and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] The preparation of embodiment 1,2-(3-phenyl)-4-imino-3,4-dihydroquinazoline)-2-aniline (structural formula (II))

[0036]

[0037] Into a 25mL sealed tube, add 2-aminobenzonitrile (2.0mmol, 236mg), diphenyl hypervalent iodine hexafluorophosphate (1.0mmol, 426mg), replace nitrogen three times, add 1,2-dichloroethane alkanes (3 mL). The system was stirred at room temperature for 15-30 minutes to make the system evenly mixed, and the sealed tube was moved into an oil bath at 120°C to react for 2 days. After the reaction, the system was cooled to room temperature. Add 3mL of methanol, potassium carbonate (1mmol, 138mg), 2 drops of deionized water to the system, and stir at room temperature for 3-5h. The system solution was concentrated and spin-dried to obtain a crude product. The crude product was separated by column chromatography (200-300 mesh silica gel) with ethyl acetate:petroleum ether:triethylamine=5:3:1 as the eluent, and the milky white solid product 2-(3- ...

Embodiment 2

[0044] Embodiment 2, the preparation of 2-(3-(4-methylbenzene)-4-imino-3,4-dihydroquinazoline)-2-aniline (structural formula (III))

[0045]

[0046] Into a 25mL sealed tube, add 2-aminobenzonitrile (2.0mmol, 236mg), bis(3-methyl-phenyl) hypervalent iodine hexafluorophosphate (1.0mmol, 426mg), replace nitrogen three times, add 1,2-Dichloroethane (3 mL). The system was stirred at room temperature for 15-30 minutes to make the system evenly mixed, and the sealed tube was moved into an oil bath at 120°C to react for 2 days. After the reaction, the system was cooled to room temperature. Add 3mL of methanol, potassium carbonate (1mmol, 138mg), 2 drops of deionized water to the system, and stir at room temperature for 3-5h. The system solution was concentrated and spin-dried to obtain a crude product. The crude product was separated by column chromatography (200-300 mesh silica gel) with ethyl acetate:petroleum ether:triethylamine=5:3:1 as eluent, and the brown solid product 2...

Embodiment 3

[0053] Embodiment 3, the preparation of 2-(3-(3-methylbenzene)-4-imino-3,4-dihydroquinazoline)-2-aniline

[0054] Into a 25mL sealed tube, add 2-aminobenzonitrile (2.0mmol, 236mg), bis(3-methyl-phenyl) hypervalent iodine hexafluorophosphate (1.0mmol, 426mg), replace nitrogen three times, add 1,2-Dichloroethane (3 mL). The system was stirred at room temperature for 15-30 minutes to make the system evenly mixed, and the sealed tube was moved into an oil bath at 120°C to react for 2 days. After the reaction, the system was cooled to room temperature. Add 3mL of methanol, potassium carbonate (1mmol, 138mg), 2 drops of deionized water to the system, and stir at room temperature for 3-5h. The system solution was concentrated and spin-dried to obtain a crude product. The crude product was separated by column chromatography (200-300 mesh silica gel) with ethyl acetate:petroleum ether:triethylamine=5:3:1 as eluent, and the yellow solid product 2-(3- Preparation of (3-methylbenzene)...

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 polysubstituted quinazoline imine derivative and a preparation method thereof, belonging to the technical field of chemicals preparation. The structural formula of the polysubstituted quinazoline imine derivative is shown in a formula (I). The preparation method comprises the step as follows: carrying out a heating reaction on diaryl hypervalent iodine salt and o-aminoacrylonitrile in a solvent under the catalysis of a copper salt for 2-24 hours at 70-150 DEG C to obtain the polysubstituted quinazoline imine derivative shown in the formula (I). The synthesis method of the polysubstituted quinazoline imine derivative disclosed by the invention is scientific and reasonable; the polysubstituted quinazoline imine derivative with various substituent groups, which cannot be synthesized by other methods, can be synthesized; the preparation method has the characteristics of simple synthesis process, high productive rate and the like; and the polysubstituted quinazoline imine derivative is easy to purify.

Description

technical field [0001] The invention belongs to the technical field of chemical medicine preparation, and in particular relates to a polysubstituted quinazoline imine derivative and a preparation method thereof. Background technique [0002] Quinazoline imine compounds have shown good biological activity in pesticides and medicines, and have become a hot spot of common research by scholars in the fields of chemistry and biology. In terms of medicine, it can inhibit the EGF receptor (EGFR), and then exhibit high anticancer activity. In addition, quinazoline compounds also have anti-malarial, anti-tumor and anti-HIV activities; they also have a great effect on the treatment of benign prostatic hyperplasia and hypertrophy; as α-receptor blockers, they occupy an important role in the prevention and treatment of cardiovascular diseases. Very important role; very effective in preventing atherosclerosis and coronary heart disease. In terms of pesticides, especially quinazoline ox...

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): C07D239/94
CPCC07D239/94
Inventor 陈超庞鑫龙
Owner TSINGHUA UNIV
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products