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

Preparation method of polysubstituted pyrrole compound

A compound and multi-substitution technology, which is applied in the field of preparation of multi-substituted pyrrole compounds, achieves the effects of good compatibility, mild reaction conditions and simple operation

Active Publication Date: 2019-06-07
ZHEJIANG NORMAL UNIVERSITY
View PDF2 Cites 4 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The traditional radical addition reaction of this type mainly relies on the reductive radical addition to the carbon-nitrogen double bond. However, the oxidative radical addition of the carbon-nitrogen double bond still faces many challenges.

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 polysubstituted pyrrole compound
  • Preparation method of polysubstituted pyrrole compound
  • Preparation method of polysubstituted pyrrole compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Take a dry reaction tube, weigh into silver trifluoroacetate (5.5 mg, 0.025 mmol), ammonium persulfate (171.2 mg, 0.75 mmol) and then add N-(4-cyano Benzene)-aniline 1a (51.6mg, 0.25mmol) and 1-(4-methoxyphenyl)cyclopropanol (82.1mg, 0.5mmol) solution to form a reaction system. The system was reacted under nitrogen, stirred at 50°C for 10 h, quenched by adding 10 mL of water, extracted three times with ethyl acetate (10 mL), combined, the organic phase was washed with saturated edible water, and dried over anhydrous sodium sulfate. The organic phase was concentrated and separated by silica gel (300-400 mesh) column chromatography to obtain 87.6 mg of yellow solid 3aa with a yield of 86%.

[0027] Product Spectrum Analysis 1 H NMR (600MHz, CDCl 3 )δ7.41(d, J=8.3Hz, 2H), 7.33–7.26(m, 3H), 7.10(d, J=8.0Hz, 2H), 7.03(d, J=7.5Hz, 2H), 6.97( d,J=7.8Hz,2H),6.73(d,J=8.5Hz,2H),6.59(d,J=3.1Hz,1H),6.43(d,J=3.4Hz,1H),3.75(s, 3H); 13 C NMR (151MHz, CDCl 3 )δ158.5, 138.5, 137.7...

Embodiment 2

[0031] Except that the N-(4-cyanobenzylene)-aniline shown in the structural formula 1a in Example 1 is replaced with the N-benzylaniline shown in the structural formula 1b, all the other operating steps are the same as in Example 1, and the yield: 65%, White solid 3ba. Product Spectrum Analysis 1 H NMR (600MHz, CDCl 3 )δ7.23–7.21(m,3H),7.15–7.14(m,2H),7.13–7.10(m,1H),7.07–7.04(m,2H),7.02(m,2H),6.98(m, 2H), 6.71(m, 2H), 6.48–6.45(m, 1H), 6.41(m, 1H), 3.74(d, J=0.8Hz, 3H); 13 C NMR (151MHz, CDCl 3)δ158.1, 139.0, 135.7, 135.2, 133.3, 130.0, 128.9, 128.7, 128.6, 127.8, 127.1, 126.1, 125.9, 113.3, 109.7, 109.2, 55.1; HRMS (ESI) calcd for C 23 h 19 NONa[M+Na] + 348.1359, found 348.1353.

[0032] The reaction formula is as follows:

[0033]

Embodiment 3

[0035] Except that N-(4-chlorobenzene)-aniline shown in structural formula 1c is used to replace N-(4-cyanobenzene)-aniline shown in structural formula 1a in Example 1, all the other operating steps are the same as in Example 1, Yield: 68%, 3ca as a white solid.

[0036] Product Spectrum Analysis 1 H NMR (600MHz, CDCl 3 )δ7.24(d, J=6.3Hz, 3H), 7.11(d, J=8.4Hz, 2H), 7.02–6.99(m, 2H), 6.96(t, J=7.9Hz, 4H), 6.71( d, J=8.6Hz, 2H), 6.45(d, J=3.5Hz, 1H), 6.39(d, J=3.5Hz, 1H), 3.73(s, 3H); 13 C NMR (151MHz, CDCl 3 )δ158.2, 138.7, 136.1, 133.9, 131.9, 131.8, 130.0, 129.6, 128.8, 128.0, 127.3, 125.6, 113.4, 110.0, 109.3, 55.1; HRMS (ESI) calcd for C 23 h 18 NClNa[M+Na] + 382.0969, found 482.0967.

[0037] The reaction formula is as follows:

[0038]

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 preparation method of a polysubstituted pyrrole compound. The preparation method comprises the following steps: mixing imine shown as a formula II, cyclopropanol shown as a formula III, a catalyst, an oxidant and a solvent to form a reaction system; after the reaction is finished, carrying out post-treatment to obtain the polysubstituted pyrrole compound with the structure shown in the formula I. According to the preparation method, a free radical oxidation addition strategy is applied to the imine compound for the first time, a novel [3+2] cycloaddition reaction is ingeniously constructed, direct C-H activation of the imine compound is achieved, and the polysubstituted pyrrole compound is generated in one step. The method has the advantages of mild reaction conditions, simple operation, good functional group compatibility, wide substrate applicability, good reaction yield, good theoretical value and good application prospect.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a preparation method of polysubstituted pyrrole compounds. Background technique [0002] Pyrrole is an important class of five-membered nitrogen-containing heterocyclic compounds. It is a common structural unit of natural products and a very important class of compounds in a large number of natural products. Compounds containing pyrrole rings exhibit various physiological activities. It has extremely wide application value in material science and is often used as a raw material in organic synthesis, medicine, pesticides, spices, rubber vulcanization accelerators, epoxy resin curing agents, etc. Multi-substituted pyrrole and its derivatives are an important class of fine chemical intermediates widely used in medicine, pesticides, daily chemicals, coatings, textiles, printing and dyeing, and many other fields. Studies have shown that many polysubstituted pyrroles and t...

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): C07D207/333C07D207/337C07D401/04
Inventor 朱钢国吴明昌谢佳燕罗芳
Owner ZHEJIANG 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