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

Tetrahydrodiazepine and quinazoline compounds and preparation method thereof

A compound and quinoline technology, applied in the field of heterocyclic quinoline compounds and their preparation, to achieve the effects of high diastereoselectivity and enantioselectivity, mild reaction conditions and few side reactions

Active Publication Date: 2018-02-13
CHINA AGRI UNIV
View PDF3 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although there have been many reports on the synthesis methods of heterocyclic quinolines, the synthesis of seven-membered heterocyclic quinolines, especially the synthesis of optically active heterocyclic quinolines by [4+3] cyclization blank

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
  • Tetrahydrodiazepine and quinazoline compounds and preparation method thereof
  • Tetrahydrodiazepine and quinazoline compounds and preparation method thereof
  • Tetrahydrodiazepine and quinazoline compounds and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027]

[0028] Put 0.0374g (0.125mmol) of compound 1a, 0.0384g (0.190mmol) of compound 2a and 2mL of dichloromethane into a dry 15mL Shrek tube, add 6.6mg (0.025mmol) of triphenylphosphine and mix well for cycloaddition into a reaction. In this reaction system, the molar ratio of compound 1a to compound 2a is 1: 1.5, and organophosphorus catalyst I accounts for 20% of the molar percentage of compound 1a, stirs at 25 ℃ for 6 hours, and concentrates through the column with rotary evaporator (acetic acid Ethyl ester:petroleum ether=1:4, v / v), to obtain 50.0 mg of product 3aa, with a yield of 80%.

Embodiment 2

[0030]

[0031] Put 0.0374g (0.125mmol) of compound 1a, 0.0384g (0.190mmol) of compound 2a and 2mL of dichloromethane into a dry 15mL Shrek tube, add 0.025mmol of trimethylphosphine and mix well for cycloaddition reaction. In this reaction system, the molar ratio of compound 1a to compound 2a is 1: 1.5, and organophosphorus catalyst I accounts for 20% of the molar percentage of compound 1a, stirs at 25 ℃ for 6 hours, and concentrates through the column with rotary evaporator (acetic acid Ethyl ester:petroleum ether=1:4, v / v), to obtain 21.9mg of product 3aa, yield 35%.

Embodiment 3

[0033]

[0034] Put 0.0374g (0.125mmol) of compound 1a, 0.0384g (0.190mmol) of compound 2a and 2mL of dichloromethane into a dry 15mL Shrek tube, add 0.025mmol of tributylphosphine and mix well for cycloaddition reaction. In this reaction system, the molar ratio of compound 1a to compound 2a is 1: 1.5, and organophosphorus catalyst I accounts for 20% of the molar percentage of compound 1a, stirs at 25 ℃ for 3 hours, and concentrates through the column with rotary evaporator (acetic acid Ethyl ester:petroleum ether=1:4, v / v), to obtain 25.0mg of product 3aa, yield 40%.

[0035] It can be seen that the effect is very excellent when triphenylphosphine is selected as the catalyst.

[0036] 3aa NMR

[0037]1 H NMR (300MHz, CDCl 3 )δ7.85-7.72 (m, 2H), 7.43 (dd, J = 9.1, 3.4Hz, 1H), 7.37-7.26 (m, 7H), 7.17 (td, J = 7.6, 1.5Hz, 1H), 7.06 (td, J=7.5, 1.4Hz, 1H), 7.00 (dd, J=7.8, 1.3Hz, 1H), 6.89(s, 1H), 6.80 (dd, J=7.6, 1.5Hz, 1H), 6.05( d, J=0.8 Hz, 1H), 4.92(d, J=10.3Hz, 1H), ...

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 novel tetrahydrodiazepino quinazoline compound and a preparation method thereof.The structural formula of the tetrahydro-diazepino-quinazoline compound is shown as 3 or 4 (Please see the chemical formula in the description.), wherein R1 is selected from C1-20 alkyl, H, F, C1, Br or C1-20 alkoxy, NO2, CN, SO3H, phenyl or substituted phenyl and five-membered heterocycleyl or C1-20 naphtheneyl, and R2 is selected from C1-20 alkyl, benzyl or substituted benzyl, pheterocycle quinazolinehenyl or substituted phenyl and naphthyl or substituted naphthyl.

Description

technical field [0001] The invention relates to a class of heterocyclic quinoline compounds and a preparation method thereof. Background technique [0002] Quinazoline compounds are the main framework of many natural alkaloids, a class of nitrogen-containing heterocyclic compounds with good biological activity, and have been widely used in the fields of pesticides and medicine. It has anticancer, antitumor, antibacterial, antiviral, antituberculosis and other pharmacological effects (J.Med.Chem.1996,39,5176.; J.Med.Chem.2000,43,1910.; Farmaco2000,55 , 725.; ActaPhys.-Chim.Sin.2006, 22, 1372.; Antiviral Res.2007, 74, 34.; Eur.J.Med.Chem.2009, 44, 3046.; Chem.Pharm.Bull. 2009 , 57, 580.; J.Chromatogr., B 2010, 878, 1285.), some quinazoline compounds have been successfully commercialized, such as the fungicide fluquinazole, the acaricide fenazaquin, and the anticancer drug Yirui sand etc. And heterocyclic quinoline compounds are also a class of biologically active molecules,...

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 Patents(China)
IPC IPC(8): C07D487/04
CPCC07D487/04
Inventor 郭红超袁春浩周磊杰王博
Owner CHINA AGRI 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