Synthesis method of pyrano[4,3-b] pyridine-2,7-dione compound

A synthetic method and compound technology, applied in the direction of organic chemistry, can solve the problems of unsuitability for large-scale production, increased by-products, low yield, etc., and achieve good market prospects, less side reactions, and easy operation.

Active Publication Date: 2021-11-02
INST OF APPLIED CHEM JIANGXI ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the methods reported in the current public literature still have certain restrictions on the source of reaction raw materials (especially in multi-component reactions), and there are many steps, resulting in increased by-products, low yields or cumbersome operations, and are not suitable for large-scale production. and other shortcomings

Method used

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  • Synthesis method of pyrano[4,3-b] pyridine-2,7-dione compound
  • Synthesis method of pyrano[4,3-b] pyridine-2,7-dione compound
  • Synthesis method of pyrano[4,3-b] pyridine-2,7-dione compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Compound 4-amino-2-pyrone Compound A 1 (1mmol, 0.26g), dimethyl butynedioate B 1 (1.5mmol, 0.18mL) and 0.1 times the amount of copper trifluoromethanesulfonate (0.1mmol, 0.03g) were placed in a 25mL round bottom flask, added toluene (8mL) to dissolve, stirred evenly, and reacted at a temperature of 80°C 6 hours, TLC monitoring, until reaction substrate A 1 disappear; after the reaction, pour the reaction solution into 20mL saturated sodium chloride solution, stir, extract three times with dichloromethane (3×20mL), separate the liquids, and combine the organic phases; the organic phases are washed with anhydrous MgSO 4 Drying, evaporation of the solvent under reduced pressure, separation by column chromatography, the eluent is petroleum ether / acetone, the volume ratio of petroleum ether and acetone is 5:1, and the target compound C is obtained as a white solid 1 , and the yield was 87%.

[0028] The specific reaction formula is:

[0029]

[0030] For compound C 1...

Embodiment 2

[0032] Compound 4-amino-2-pyrone Compound A 2 (1mmol, 0.17g), dimethyl butynedioate B 1 (1.5mmol, 0.18mL) and 0.1 times the amount of copper acetate (0.1mmol, 0.02g) were placed in a 25mL round-bottomed flask, added xylene (6mL) to dissolve, stirred well, and reacted at 100°C for 5 hours. TLC monitoring, until reaction substrate A 2 disappear; after the reaction, pour the reaction solution into 20mL saturated sodium chloride solution, stir, extract three times with dichloromethane (3×20mL), separate the liquids, combine the organic phases; use anhydrous NaSO 4 Dry, evaporate the solvent under reduced pressure, and separate by column chromatography, the eluent is petroleum ether / acetone, the volume ratio of petroleum ether and acetone is 5:2, and the target compound C is obtained as a white solid 2 , the yield was 83%.

[0033] The specific reaction formula is:

[0034]

[0035] For compound C2 Proton NMR detection: White solid; m.p.95-97°C; 1 HNMR (CDCl 3 ,400MHz)δ: 1...

Embodiment 3

[0037] Compound 4-amino-2-pyrone Compound A 3 (1mmol, 0.24g), methyl 2-butynoate B 2 (1.2mmol, 0.12mL) and 0.13 times the amount of copper bromide (0.13mmol, 0.03g) were placed in a 25mL round bottom flask, added 1,2-dichloroethane (5mL) to dissolve, stirred evenly, and Reaction at ℃ temperature for 7 hours, TLC monitoring, until reaction substrate A 3 disappear; after the reaction, pour the reaction solution into 20mL saturated sodium chloride solution, stir, extract three times with dichloromethane (3×20mL), separate the liquids, combine the organic phases; use anhydrous NaSO 4 Drying, evaporation of the solvent under reduced pressure, separation by column chromatography, the eluent is petroleum ether / ethyl acetate, the volume ratio of petroleum ether and ethyl acetate is 6:1, and the target compound C is obtained as a white solid 3 , the yield was 79%.

[0038] The specific reaction formula is:

[0039]

[0040] For compound C 3 Proton NMR detection: White solid; m....

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Abstract

The invention discloses a synthesis method of a pyrano[4,3-b] pyridine-2,7-dione compound, wherein the synthesis method comprises the steps: dissolving a 4-amino-2-pyranone compound and an acetylenic acid ester compound as raw materials and a copper salt as a catalyst in an organic solvent, and carrying out cyclization reaction to obtain the pyrano[4,3-b] pyridine-2,7-dione compound. The method has the advantages of few reaction steps, single product structure, few side reactions, high yield and good market prospect.

Description

technical field [0001] The invention belongs to the technical field of compound synthesis, and in particular relates to a synthesis method of pyrano[4,3-b]pyridine-2,7-dione compound. Background technique [0002] Pyranopyridine derivatives are important heterocyclic structural units, and a variety of molecules containing this structural unit exhibit important biological and pharmacological activities, such as antifungal, antitumor, antiviral, antimycobacterial activity, antivasodilation activity, neurotropic activity and anti-angiogenic activity, etc., so it has a wide range of applications in medicine and other related fields. In view of the importance of this type of compound, its synthesis research has also received extensive attention, and a variety of synthetic methods have been developed one after another. [0003] Selvam et al. under solvent-free conditions, using SnCl 2 2H 2 O catalyzed the Friedlander reaction of 2-amino-3-cyano-4H-pyran with cyclopentanone or c...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/052
CPCC07D491/052
Inventor 胡居吾韩晓丹王慧宾
Owner INST OF APPLIED CHEM JIANGXI ACAD OF SCI
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