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

Preparation method of tryptopquinoline heterocyclic compound

A technology of heterocyclic compounds and quinoline, which is applied in the field of organic synthesis, can solve the problems of no chromonoquinoline heterocyclic compounds and cumbersome preparation methods, and achieve the effects of simple reaction, simple operation and low cost

Active Publication Date: 2019-06-28
SUZHOU UNIV
View PDF0 Cites 2 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] Chromone and quinoline heterocyclic compounds (12 H -chromeno[2,3- b ]quinolin-12-one and 6 H -chromeno[4,3- b ]quinolin-6-one) are two common chromonoquinoline heterocyclic structures, both of which are a pair of positional isomers; in the prior art, the preparation methods of chromonoquinoline heterocyclic compounds are mostly cumbersome
Anthranilic anhydride is a structure containing a 2,1-benzisoxazole heterocycle, which often participates in the reaction as a bifunctional reagent under the catalysis of various metals, but there is no preparation of chromonoquinoline heterocyclic compounds from anthranilic anhydride report

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 tryptopquinoline heterocyclic compound
  • Preparation method of tryptopquinoline heterocyclic compound
  • Preparation method of tryptopquinoline heterocyclic compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021]

[0022] In a 15 mL tube were added anthranilic anhydride 1 (60 mg, 0.5 mmol) and 4-hydroxycoumarin 2a (0.65 mmol), followed by DMI (0.75 mL); the resulting mixture was then warmed to 230 °C React for 1 hour; stop heating after the reaction is over, cool to room temperature, add water and ethyl acetate, then wash the organic phase three times with water, combine the aqueous phase, extract the aqueous phase once with ethyl acetate, finally combine the organic phase, wash through anhydrous sulfuric acid After sodium drying, the solvent was evaporated under reduced pressure, and the residue was separated and purified by silica gel column chromatography to obtain products 3a and 4a respectively, with a total yield of 69%, 3a:4a=1.4:1. 3a: 1 H NMR (400 MHz, CDCl 3 ) δ: 9.29 (s, 1H), 8.41-8.30 (m, 1H), 8.16-8.03 (m, 2H), 7.92 (t, J =7.6 Hz, 1H), 7.64 (t, J = 7.5 Hz, 1H), 7.30 (d, J = 9.0 Hz, 1H), 7.15 (t, J =7.9 Hz, 1H); 13 C NMR (151 MHz, CDCl 3 ) δ: 177.02, 167...

Embodiment 2

[0024]

[0025] Into a 15 mL tube were added anthranilide 1 (60 mg, 0.5 mmol) and 4-hydroxycoumarin 2a (0.05 mmol), followed by DOA (0.75 mL). The reaction mixture was warmed up to 300 °C for 0.2 hours. Stop heating, cool to room temperature, add water and ethyl acetate. The organic phase was washed three times with water, the aqueous phase was combined, and the aqueous phase was extracted once with ethyl acetate. Finally, the organic phase was combined, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was separated and purified by silica gel column chromatography to obtain the product 3a and 4a, the total yield is 55% (based on 4-hydroxycoumarin), 3a:4a = 1.2:1.

Embodiment 3

[0027]

[0028] Anthranilide 1 (60 mg, 0.5 mmol) and 4-hydroxycoumarin 2a (5 mmol) were added to a 15 mL tube, followed by DMI (5 mL). The reaction mixture was warmed up to 150°C for 5 hours. Stop heating, cool to room temperature, add water and ethyl acetate. The organic phase was washed three times with water, the aqueous phase was combined, and the aqueous phase was extracted once with ethyl acetate. Finally, the organic phase was combined, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was separated and purified by silica gel column chromatography to obtain the product 3a and 4a, the total yield is 63%, 3a:4a = 1.3:1.

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 of preparing a tryptopquinoline heterocycle by carrying out a heating reaction on anthranil and 4-hydroxyl coumarin. The reaction comprises the following steps: dissolving anthranil and 4-hydroxyl coumarin in a solvent, and carrying out a reaction on the reaction mixture at 150-300 DEG C for 0.2-5 hours; and stopping heating, cooling the reactant to room temperature, adding water, extracting the reactant with a solvent, evaporating the reactant, carrying out purification by a column chromatography to obtain the tryptopquinoline heterocyclic compound. The preparation method is the reaction of anthranil and 4-hydroxyl coumarin in a thermal promoting condition. Catalysts and additives are not needed for the conversions, few byprodcuts are available, and the preparation method is a novel method of constructing the tryptopquinoline heterocyclic compound quickly.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a method for preparing chromonoquinoline heterocyclic compounds by reacting anthranilide and 4-hydroxycoumarin at high temperature. Background technique [0002] Chromone and quinoline heterocyclic compounds (12 H -chromeno[2,3- b ]quinolin-12-one and 6 H -chromeno[4,3- b ]quinolin-6-one) are two common chromonoquinoline heterocyclic structures, both of which are a pair of positional isomers; in the prior art, the preparation methods of chromonoquinoline heterocyclic compounds are mostly cumbersome . Anthranilic anhydride is a structure containing a 2,1-benzisoxazole heterocycle, which often participates in the reaction as a bifunctional reagent under the catalysis of various metals, but there is no preparation of chromonoquinoline heterocyclic compounds from anthranilic anhydride reports. Contents of the invention [0003] The technical problem to b...

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): C07D491/052
Inventor 张士磊毛玉健胡延维孙婉婉陈韶华
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