Unlock instant, AI-driven research and patent intelligence for your innovation.

A kind of synthetic method of 3-alkynylpyrrole compound

A technique for the synthesis of alkynylpyrrole and a synthesis method, which is applied in the field of synthesis of 3-alkynylpyrrole compounds, can solve the problems of limitation, poor regioselectivity, cumbersome operation, etc., and achieve the effects of simple raw materials, easy operation, and simple synthesis process

Active Publication Date: 2021-08-24
HENAN NORMAL UNIV
View PDF2 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It should be pointed out that although the alkynyl-substituted pyrrole has important research and application value, the current reliable methods for the synthesis of such compounds are very limited, and these methods often have disadvantages such as poor regioselectivity and cumbersome operations.

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 3-alkynylpyrrole compound
  • A kind of synthetic method of 3-alkynylpyrrole compound
  • A kind of synthetic method of 3-alkynylpyrrole compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023]

[0024] Add 1a (0.5mmol, 81mg), acetonitrile (5mL), anhydrous copper acetate (1mmol, 181mg), iodine (0.5mmol, 127mg) and 4-dimethylaminopyridine (DMAP, 0.5 mmol, 61 mg), vacuumized and filled with oxygen (1 atm), placed in an oil bath at 80°C and stirred for 10 h. Then, 10 mL of saturated brine was added to quench the reaction, extracted with ethyl acetate (10 mL×3), and the organic phases were combined and dried over anhydrous sodium sulfate. Filter, spin dry, and separate through silica gel column (petroleum ether / ethyl acetate=100 / 1) to obtain compound 2a (87mg, 65%). Compound 2a (0.3mmol, 81mg), phenylacetylene (4a, 0.9mmol, 92mg), palladium acetate (0.015mmol, 3.4mg), pivalic acid (0.3mmol, 31mg), PPh 3 (0.03mmol, 7.8mg), tetrabutylammonium bromide (0.3mmol, 97mg), potassium carbonate (0.3mmol, 41mg) and DMF (5mL) were placed in a 10mL Shrek tube, vacuumed and flushed with nitrogen, and then the reaction The system was heated up to 90°C and reacted for 20 hou...

Embodiment 2

[0026] Add 1a (0.5mmol, 81mg), acetonitrile (5mL), anhydrous copper acetate (0.5mmol, 91mg), iodine element (0.125mmol, 32mg) and DMAP (0.5mmol, 61mg) to a 10mL Shrek tube successively, and draw After inflating oxygen (1 atm) under vacuum, it was placed in an oil bath at 80° C. and stirred for 10 h. Then, 10 mL of saturated brine was added to quench the reaction, extracted with ethyl acetate (10 mL×3), and the organic phases were combined and dried over anhydrous sodium sulfate. Filter, spin dry, and separate through silica gel column (petroleum ether / ethyl acetate=100 / 1) to obtain compound 2a (34 mg, 25%). According to the method of Example 1, 2a can be transformed into 3a.

Embodiment 3

[0028] Add 1a (0.5mmol, 81mg), acetonitrile (5mL), anhydrous copper acetate (0.5mmol, 91mg), iodine element (0.25mmol, 64mg) and DMAP (0.5mmol, 61mg) to a 10mL Shrek tube successively, and draw After inflating oxygen (1 atm) under vacuum, it was placed in an oil bath at 80° C. and stirred for 10 h. Then, 10 mL of saturated brine was added to quench the reaction, extracted with ethyl acetate (10 mL×3), and the organic phases were combined and dried over anhydrous sodium sulfate. Filter, spin dry, and separate through silica gel column (petroleum ether / ethyl acetate=100 / 1) to obtain compound 2a (69 mg, 51%). According to the method of Example 1, 2a can be transformed into 3a.

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 3-alkynylpyrrole compounds, belonging to the technical field of organic synthesis. N-substituted piperidine 1 is added to the solvent, and in the presence of copper acetate, 4-dimethylaminopyridine and additive 1, the reaction is heated in oxygen to obtain iodopyrrole compound 2, and then compound 2 and aryl alkyne 4, In the presence of palladium salts, ligands, additives 2 and a base, the reaction is heated to obtain 3-alkynylpyrrole compound 3. The method synthesizes iodopyrrole compounds through a series of series reactions of N-substituted piperidine compounds, and then couples with alkynes to obtain 3-alkynylpyrrole compounds. It provides an economical, practical and environmentally friendly new method for the synthesis of 3-alkynylpyrrole compounds.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a synthesis method of 3-alkynylpyrrole compounds. Background technique [0002] As an important class of nitrogen-containing heterocycles, pyrrole structural units are ubiquitous in natural products (such as chlorophyll, hemoglobin, hormones, pigments, pheromones and antibiotics, etc.). In addition, many artificially designed and synthesized pyrrole derivatives have become widely used drugs (such as tolmetin, atometin, sunitinib, atorvastatin, etc.), fluorescent materials and other functional materials. Therefore, the synthesis and application of pyrrole compounds is an important research content in the fields of synthetic chemistry, medicinal chemistry and biochemistry. [0003] On the other hand, the alkynyl group is one of the most important organic functional groups with various important reactivity properties. Starting from the alkynyl group, various ...

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 Patents(China)
IPC IPC(8): C07D207/323C07D207/325
CPCC07D207/323C07D207/325
Inventor 范学森王芳张新迎何艳
Owner HENAN NORMAL UNIV