Check patentability & draft patents in minutes with Patsnap Eureka AI!

Polysubstituted sulfo-pyrrolidone derivative synthesis method

A technology of thiopyrrolidone and synthesis method, applied in the direction of organic chemistry and the like, can solve problems such as weak acidity, and achieve the effects of short reaction time, high reaction efficiency and strong catalytic activity

Inactive Publication Date: 2016-08-24
XUZHOU NORMAL UNIVERSITY +2
View PDF0 Cites 4 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the weak acidity of phenols, a strong electron-withdrawing group (such as nitro) is generally required at the adjacent or para-position of the hydroxyl group. Therefore, there are few reports on Ugi reactions involving heterocyclic thiols with relatively weak acidity and low activity.

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 sulfo-pyrrolidone derivative synthesis method
  • Polysubstituted sulfo-pyrrolidone derivative synthesis method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment Construction

[0030] To synthesize (3-benzoxazol[D]-2-yl)-1-phenyl-2-amino-4-(4-iodophenyl)-5-2-mercapto-dihydro-hydropyrrole-3 - Nitrile as an example

[0031] Add 23.1mg of the substrate p-iodobenzaldehyde, 7.9mg of malononitrile, 13.0mg of cyclohexyl isonitrile, and 15.1mg of 2-mercaptobenzoxazole into a 250mL round-bottomed flask, which is pre-added with 100ml of acetonitrile and water 3:1 (volume ratio) mixture. Add nano CeO 2 Catalyst 10 mg, stirred at 10°C for 12 hours, after the reaction was completed, the crude product was filtered with CH 2 Cl 2 Dissolve the crude product and centrifuge (4000r / min, 20min) to obtain nanometer CeO 2 solid, CeO 2 The solid is washed with ethanol for 2-3 times, dried under an infrared lamp and reused for catalytic reaction, which can be reused for 2-3 times. The liquid portion was recrystallized to give the product 3-benzoxazol[D]-2-yl)-1-phenyl-2-amino-4-(4-iodophenyl)-5-2-mercapto-dihydro- The pure product of hydropyrrole-3-carbonitrile was 4...

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 polysubstituted sulfo-pyrrolidone synthesis method. According to the method, aldehyde, malononitrile, cyclohexyl isocyanide and faintly acid mercaptobenzoxazole or thiazole are mixed for one-step reaction under the catalysis of nanometer CeO2 to obtain a sulfo-pyrrolidone derivative. According to the synthesis method, nanometer CeO2 is used as a catalyst and is stable, capable of being repeatedly used, small in usage amount and high in efficiency compared with traditional methods, and the requirement of green chemistry is met; nanometer CeO2 is high in the catalytic activity and wide in application range, and is more suitable for aromatic aldehyde containing electrondrawing groups compared with traditional methods. Faintly acid heterocyclic thione with low activity is used as a substrate, the sulfo-pyrrolidone derivative with diversified structures is synthesized through multi-component Ugi-Smiles cascade reaction, the reaction condition is mild, heating is not needed, reaction time is short, yield is high, and aftertreatment is convenient.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, in particular to a new synthesis method of polysubstituted thiopyrrolidones. Background technique [0002] Pyrrolidone derivatives are an important class of organic heterocyclic compounds, which widely exist in nature. Compounds with pyrrolidone as the skeleton have potential pharmacological and biological activities. Pyrrolidine derivatives play an important role in the growth and development of objects, energy conversion, information transmission, etc., such as anti-inflammatory, anti-tumor, immunosuppressant, etc. , among which atorvastatin calcium has brought great repercussions. Due to the biological activity of this type of compound, this type of compound has been extensively studied in medicine, pesticide, biological research and the like. [0003] In recent years, with the in-depth research on heterocyclic drugs, especially the synthesis of various substituted pyrrolidin-2-on...

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): C07D413/04
Inventor 陈才法王园江刘贵香韩锡光宛瑜吴翚
Owner XUZHOU NORMAL UNIVERSITY
Features
  • R&D
  • Intellectual Property
  • Life Sciences
  • Materials
  • Tech Scout
Why Patsnap Eureka
  • Unparalleled Data Quality
  • Higher Quality Content
  • 60% Fewer Hallucinations
Social media
Patsnap Eureka Blog
Learn More

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2025 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com