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Polysubstituted pyrrole compound and synthesis method thereof

A synthetic method and compound technology, applied in the field of multi-substituted pyrrole compounds and their synthesis

Active Publication Date: 2021-05-28
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Under the catalysis of metal rhodium, nitrogen heterocycles are prone to unimolecular alkene insertion reactions on nitrogen heterocycles [1 -4], there is no report on the formation of polysubstituted pyrrole compounds through bimolecular alkenes

Method used

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  • Polysubstituted pyrrole compound and synthesis method thereof
  • Polysubstituted pyrrole compound and synthesis method thereof
  • Polysubstituted pyrrole compound and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025]

[0026] The specific process is: weigh (2a) (86mg, 0.3mmol), (3a) (134mg, 0.75mmol), dichloro(pentamethylcyclopentadienyl) rhodium (III) dimer (4mg , 0.006mmol) and copper acetate (109mg, 0.6mmol) were placed in a 25mL Schlenk reaction flask, 3mL of dichloroethane was added, and the reaction was stirred at 110°C for 24 hours. After the reaction, the volatile components were removed under reduced pressure, and then separated by silica gel column chromatography (eluent was petroleum ether (60-90°C) / ethyl acetate, v / v=20:1) to obtain the white solid target Product (1a) (169 mg, 88% yield). The target product was confirmed by NMR and high-resolution mass spectrometry.

[0027] Compound Characterization Data

[0028] Polysubstituted pyrrole (1a): yellow liquid, 1 H NMR (400MHz, CDCl 3 )δ8.00(d,J=7.6Hz,1H,aromatic CH),7.76(m,2H,aromatic CH),7.39(m,9H,aromatic CH),7.18(s,5H,aromatic CH),7.01(d , J=5.7Hz, 1H, alkenyl CH), 6.96(t, J=7.3Hz, 1H, aromatic CH), 6.85(m, 6H, ...

Embodiment 2

[0030]

[0031] The reaction steps and operation are the same as in Example 1, except that the difference from Example 1 is that the catalyst is rhodium trichloride. The reaction was stopped, and the target product (1a) (29 mg, yield 15%) was obtained after post-processing.

Embodiment 3

[0033]

[0034] The reaction steps and operations are the same as in Example 1, except that the solvent is N,N-dimethylformamide. The reaction was stopped, and the target product (1a) (79 mg, yield 41%) was obtained after post-processing.

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Abstract

The invention relates to the field of synthesis of pyrrole compounds, in particular to a polysubstituted pyrrole compound and a synthesis method thereof. According to the method, inner enamine and inner alkyne are used as raw materials and are subjected to transition metal rhodium catalyzed didehydrogenation coupling reaction at high temperature, so that the polysubstituted pyrrole compound is constructed in one step. The method has the advantages of easily available raw materials, simple operation, mild synthesis reaction conditions, high efficiency, wide substrate adaptability, and diversity of functional groups.

Description

technical field [0001] The invention relates to the field of synthesis of pyrrole compounds, in particular to a multi-substituted pyrrole compound and a synthesis method thereof. Background technique [0002] Multi-substituted pyrrole can be used as a standard substance for chromatographic analysis, as well as in organic synthesis and pharmaceutical industry. It is mainly used as a solvent for polyester fiber spinning, and also as a metal preservative, epoxy resin curing agent, catalyst for olefin polymerization and Raw materials in the pharmaceutical industry, etc., are also used as photosensitizers. Under the catalysis of rhodium metal, the nitrogen heterocycle is prone to unimolecular insertion reaction on the nitrogen heterocycle [1 -4], there is no report on the formation of polysubstituted pyrrole compounds through bimolecular alkenes. Contents of the invention [0003] The object of the present invention is to provide a polysubstituted pyrrole compound and a synth...

Claims

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Application Information

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IPC IPC(8): C07D471/22
CPCC07D471/22
Inventor 余正坤李云龙
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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