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

A kind of synthetic method of furo[3,2-c]pyridin-4(5h)-one compound

A ketone compound and synthesis method technology, applied in the field of furan [3], can solve the problems of limited organic synthesis reaction, few substituents and functional groups, increase in synthesis cost, etc. cost reduction effect

Active Publication Date: 2011-12-14
CHANGZHOU INST OF ENERGY STORAGE MATERIALS &DEVICES
View PDF0 Cites 12 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the raw materials used in this method can also be produced industrially, they have not become bulk products, so the price is relatively high; the method requires at least four steps from the raw materials to the final product, and the average yield of each step is 80%. The total yield is only about 40%; the reaction conditions of this method are harsh, and antifouling and explosion-proof measures need to be taken during the synthesis process, which increases the synthesis cost
The other is to construct a furan ring through an intramolecular heterocyclization reaction on the basis of an existing pyridone ring (①J.Org.Chem.2008, 73, 8619-8622; ②Synthesis, 2010, 1741-1744), and its disadvantages The raw materials are not easy to obtain, and the catalyst is expensive
[0004] In addition, the furo[3,2-c]pyridin-4(5H)-one compounds synthesized by the existing two types of synthetic methods have few substituents and functional groups, which limits the participation of such products as intermediates in further organic synthesis reactions

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
  • A kind of synthetic method of furo[3,2-c]pyridin-4(5h)-one compound
  • A kind of synthetic method of furo[3,2-c]pyridin-4(5h)-one compound
  • A kind of synthetic method of furo[3,2-c]pyridin-4(5h)-one compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Add 10.0 mL of DMF to a 25 mL round-bottomed flask reactor equipped with a stirrer at room temperature, stir, and add 3.0 mmol of Tf dropwise to it within 5 minutes 2 O, forming DMF and Tf 2O mixture, stirred for 3 minutes. Then add 1.0 mmol of 1-(3-(dimethylamino)acryloyl)-N-p-tolylcyclopropanamide to the mixed solution to form a reaction solution, then raise the temperature to 100°C, stir for 2.5 hours, and stop the synthesis process. The reaction solution was poured into 200 ml of saturated brine, extracted three times with 60 ml of dichloromethane, combined the organic phases, washed twice with 30 ml of water, dried with 10 g of anhydrous magnesium sulfate, filtered to remove magnesium sulfate, and evaporated to remove the organic phase. The solvent and the residue were separated by silica gel column chromatography to obtain the product furo[3,2-c]pyridin-4(5H)-one with a yield of 88%. The reaction formula is as follows:

[0040]

[0041] Data characterizatio...

Embodiment 2

[0048] Add 8.0 mL of DMF to a 25 mL round-bottomed flask reactor equipped with a stirrer at room temperature, stir, and add 1.5 mmol of Tf dropwise to it within 5 minutes 2 O, forming DMF and Tf 2 O mixture, stirred for 7 minutes. Then add 1.0 mmol of 1-(3-(dimethylamino)acryloyl)-N-phenylcyclopropanamide to the mixed solution to form a reaction solution, then raise the temperature to 85°C, stir for 3.0 hours, and stop the synthesis process . The reaction solution was poured into 200 ml of saturated brine, extracted three times with 60 ml of dichloromethane, combined the organic phases, washed twice with 30 ml of water, dried with 10 g of anhydrous magnesium sulfate, filtered to remove magnesium sulfate, and evaporated to remove the organic phase. solvent, and the residue was separated by silica gel column chromatography to obtain the product furo[3,2-c]pyridin-4(5H0-one, with a yield of 95%. The reaction formula is as follows:

[0049]

Embodiment 3

[0051] Add 5.0 mL of DMF to a 25 mL round-bottomed flask reactor equipped with a stirrer at room temperature, stir, and add 2.5 mmol of Tf dropwise to it within 4 minutes 2 O, forming DMF and Tf 2 O mixture, stirred for 2 minutes. Then add 1.0 mmol of 1-(3-(dimethylamino)acryloyl)-N-phenylcyclopropanamide to the mixed solution to form a reaction solution, then raise the temperature to 70°C, stir for 2.0 hours, and stop the synthesis process . The reaction solution was poured into 200 ml of saturated brine, extracted three times with 60 ml of dichloromethane, combined the organic phases, washed twice with 30 ml of water, dried with 10 g of anhydrous magnesium sulfate, filtered to remove magnesium sulfate, and evaporated to remove the organic phase. The solvent and the residue were separated by silica gel column chromatography to obtain the product furo[3,2-c]pyridin-4(5H)-one with a yield of 91%. The reaction formula is as follows:

[0052]

[0053] Embodiment 3 and embo...

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

PropertyMeasurementUnit
Melting pointaaaaaaaaaa
Login to View More

Abstract

The invention relates to a method for synthesizing a furan[3,2-c] pyridine-4(5H) ketone compound, and belongs to the technical field of organic synthesis. The conventional synthetic method has the defects of complex synthetic steps, rigor reaction condition, high synthetic cost, low yield and few substituted groups and functional groups of the obtained products and the defect that the raw materials are not easily obtained. The method is characterized by comprising the following steps of: 1, mixing N,N-dimethylformamide (DMF) and triflate anhydride (Tf2O) at normal temperature in a molar ratioof (10-150):1, and stirring for 2 to 10 minutes; and 2, adding a cyclopropyl amide compound in an amount which is 0.3 to 1.0 molar time that of the triflate anhydride, heating to the temperature of between 70 and 120 DEG C, and stirring for 0.2 to 3.0 hours to generate the furan[3,2-c] pyridine-4(5H) ketone compound serving as a final product. The substituted groups and functional groups of the product are more, and the product can be used as an intermediate to participate in organic synthetic reaction further; and the synthetic cost is reduced substantially, and the yield is improved substantially.

Description

technical field [0001] The present invention relates to a synthetic method of furo[3,2-c]pyridin-4(5H)-ketones, which consists of N-substituted-1-(3-(dimethylamino)acryloyl)-cyclopropanamides The compound relates to the synthesis of furo[3,2-c]pyridin-4(5H)-one compounds under the reaction conditions of trifluoromethanesulfonic anhydride / DMF, and belongs to the technical field of organic synthesis. Background technique [0002] Furan[3,2-c]pyridin-4(5H)-one compounds belong to a kind of furopyridone compounds, which widely exist in natural products and have important biological and pharmaceutical activities (①Acta Chem.Scand.1998, 52, 631-634; ② J. Antibiot. 2002, 55, 6-18). [0003] The synthetic method of this class compound mainly contains two classes in the prior art: a class is to construct pyridone ring (J.Med.Chem.1989,32,1147 through multi-step traditional organic chemical reaction on the basis of existing furan ring) -1156). Although the raw materials used in thi...

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): C07D491/048
Inventor 董德文黄鹏梁永久张睿张定远
Owner CHANGZHOU INST OF ENERGY STORAGE MATERIALS &DEVICES
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