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

Method for synthesizing 3-vinyl-4-acetenyl-2,3-dihydropyrrole derivative

A technology of dihydropyrrole and ethynyl, which is applied in the direction of silicon organic compounds, chemical instruments and methods, compounds of group 4/14 elements of the periodic table, etc., can solve the problems of harsh reaction conditions and unsatisfactory yields, etc. Achieve the effect of stable performance, low cost and wide sources

Inactive Publication Date: 2018-09-07
SHANDONG UNIV OF TECH
View PDF1 Cites 5 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In this neighborhood, it has always been a challenge for scientists to directly introduce alkynes to form new carbon-carbon bonds; the traditional method for preparing alkyne compounds by organic synthesis is to use alkali metal alkyne Obviously, the reaction conditions of this kind of method are harsh, and the yield is not satisfactory; in addition, the synthesis of alkyne compounds by organometallic catalyzed coupling reaction has also been widely reported ; Like the Sonogashira cross-coupling reaction of terminal alkynes with halogenated aromatics and halogenated alkenes, it is currently a very effective method for constructing carbon-carbon bonds; developed in recent years, a class of alkynylated substances are generated by the migration of copper carbene into nitrogen hydrazone compounds; and the Heck / sonogashira chain coupling reaction of terminal alkynes and indole compounds to obtain alkyne derivatives ,and many more

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
  • Method for synthesizing 3-vinyl-4-acetenyl-2,3-dihydropyrrole derivative
  • Method for synthesizing 3-vinyl-4-acetenyl-2,3-dihydropyrrole derivative
  • Method for synthesizing 3-vinyl-4-acetenyl-2,3-dihydropyrrole derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] figure 2 ;

[0044] In a 25 mL reaction tube, the PdCl 2 (PPh 3 ) 2 (0.02 mmol), CuCl ((0.01 mmol)), K 3 PO 4 ·3H 2 O (0.4 mmol) was put in, airtight, and replaced with nitrogen three times; allenamine substrate 1a (0.2 mmol) was dissolved in dehydrated dioxane solvent (2.0 mL), and then, the solution was injected into In a closed reaction test tube; weigh the ethynyl derivative 2a (0.4mmol), at 80 o C temperature, slowly, drop by drop into the closed reaction test tube, which lasted 2.5 hours; after TLC detection, the system was cooled to room temperature; washing, extraction of organic phase, thickened silica gel spin-drying; fast column chromatography After passing the target product, 3aa (85%) was obtained as a yellow-brown liquid; 1 H NMR (400 MHz, CDCl 3 , δ ppm): 7.59 (d, J = 8.0 Hz,2H), 7.30–7.21 (m, 7H), 6.34 (s, 1H), 5.26–5.17 (m, 1H), 4.94–4.88 (m, 2H),3.66 (t, J = 10.0 Hz, 1H), 3.29–3.17 (m, 2H), 2.98 (d, J = 19.6 Hz, 1H), 2.85(d, J = 20.0 Hz...

Embodiment 2

[0046] image 3 ;

[0047] In a 25 mL reaction tube, Pd(PPh 3 ) 4 (0.02 mmol), CuCl ((0.01 mmol)), K 3 PO 4 ·3H 2 O (0.4 mmol) was put in, airtight, and replaced with nitrogen three times; allenamine substrate 1b (0.2 mmol) was dissolved in dehydrated dioxane solvent (2.0 mL), and then the solution was injected into In a closed reaction test tube; weigh the ethynyl derivative 2b (0.4mmol), at 80 o C temperature, slowly, drop by drop into the closed reaction test tube, which lasted 2.5 hours; after TLC detection, the system was cooled to room temperature; washing, extraction of organic phase, thickened silica gel spin-drying; fast column chromatography The target product was passed through to obtain brown liquid 3bb (82%); 1 H NMR (400 MHz, CDCl 3 , δ ppm): 7.68 (d, J = 7.6 Hz, 2H),7.34–7.28 (m, 4H), 7.12 (d, J = 7.6 Hz, 2H), 6.42 (s, 1H), 5.36–5.27 (m, 2H),5.03–4.98 (m, 2H), 3.76 (t, J =10.0 Hz, 1H), 3.39–3.26 (m, 2H), 3.07 (d, J =19.6 Hz, 1H), 2.94 (d, J = 2...

Embodiment 3

[0049] Figure 4 ;

[0050] In a 25 mL reaction tube, the PdCl 2 (PPh 3 ) 2 (0.02 mmol), CuCl ((0.01 mmol)), K 3 PO 4 (0.4mmol) into it, seal it, and replace it with nitrogen for 3 times; dissolve allenamine substrate 1c (0.2 mmol) in dioxane solvent (2.0 mL) except water, and then put the solution into the airtight In the reaction test tube; weigh the ethynyl derivative 2c (0.4 mmol), at 80 o C temperature, slowly, drop by drop into the closed reaction test tube, which lasted 2.5 hours; after TLC detection, the system was cooled to room temperature; washing, extraction of organic phase, thickened silica gel spin-drying; fast column chromatography The target product was passed through to obtain 3cc (77%) of yellow-brown liquid; 1 H NMR (400 MHz, CDCl 3 , δ ppm): 7.68 (d, J = 7.6 Hz, 2H), 7.33(d, J = 8.0 Hz, 4H), 6.84 (d, J = 8.0 Hz, 2H), 6.42 (s, 1H), 5.35-5.27 (m,1H), 5.03-4.98 (m, 2H), 3.81 (s, 3H), 3.75 (t, J = 10 Hz, 1H), 3.38-3.26 (m,2H), 3.06 (d, J = 19...

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 for synthesizing a 3-vinyl-4-acetenyl-2,3-dihydropyrrole derivative, and belongs to the field of chemical synthesis of allene amine cycling. The method is mainly characterized in that (1) transition metal elements are adopted for catalyzing; (2) allene is adopted as a raw material of synthesis; (3) the reaction temperature is gentle; (4) reaction is completed in one step; (5) a catalyst can be recycled and reutilized; (6) water molecules in a reaction solvent must be strictly removed, and the trace grade is achieved; (7) physical and chemical properties of a generated product cannot be changed under the environments of normal temperature and high temperature; (9) the yield of the generated product is greater than or equal to 85 weight percent; (10) a generated byproduct can be easily removed by adopting a conventional method.

Description

technical field [0001] The invention discloses a method for synthesizing 3-vinyl-4-ethynyl-2,3-dihydropyrrole derivatives, belonging to the technical field of organic compound technology application. Background technique [0002] Compounds with multifunctional pyrrole structures have attracted people's attention due to their widespread existence in natural products, bioactive molecules, material chemistry and fine chemical intermediates. Just recently, numerous biological agents and bioactive molecules have been reported one after another, and some substances have even been applied in real life; for example, bilirubin in humans, a highly efficient and selective FAP (fibroblast activation protein) inhibitor , an adrenergic receptor agonist vibegron, an orally effective FTase (Farnesyltransferase) inhibitor LB-42708, and a potent PKC (Protein KinaseC) inhibitor Go-6976, and can promote liver protein synthesis and inhibit liver hydrogen peroxide Zinc protoporphyrin with reduce...

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
Patent Type & Authority Applications(China)
IPC IPC(8): C07D207/48C07F7/08
CPCC07D207/48C07F7/0812C07F7/083Y02P20/584
Inventor 刘会梁寒冰焦鲁杨姚树志梁文静
Owner SHANDONG UNIV OF TECH
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