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Method for preparing benzofuran-pyrrole compounds by copper catalysis

A benzofuran and compound technology, applied in the field of fine chemical organic synthesis, can solve the problems of unfriendly environment, harsh reaction conditions, low product yield, etc., and achieve the effects of easy availability of raw materials and reagents, mild reaction conditions and simple operation.

Active Publication Date: 2019-01-11
XUZHOU NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

For its synthesis, there are also disadvantages such as harsh reaction conditions, low product yield, and unfriendly environment.

Method used

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  • Method for preparing benzofuran-pyrrole compounds by copper catalysis
  • Method for preparing benzofuran-pyrrole compounds by copper catalysis
  • Method for preparing benzofuran-pyrrole compounds by copper catalysis

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Embodiment 1: Preparation of benzofuran-pyrrole derivative 3a

[0029]

[0030] DCE (4 mL), 1,6-diynol-3-phenol 1a (0.278 g, 1.0 mmol) and ethyl isocyanacetate 2a (0.16 mL, 1.5 mmol) were added to a 25 mL pressure-resistant tube with a magnetic stirring device ), add cuprous iodide (0.019g, 0.1mol) and stir evenly, then put it into an 80°C oil bath and continue stirring. TLC (developing agent is V 石油醚 :V 乙酸乙酯 =3:1) The detection substrate disappears, and the reaction ends. Pour the reaction solution into saturated brine (10mL), extract with dichloromethane (3×10mL), combine the organic phases, then backwash the organic phase with saturated sodium chloride water (3×10mL), pass through anhydrous calcium chloride Steps such as drying, suction filter, vacuum distillation obtain viscous solid, finally through silica gel column chromatography (eluent is V 石油醚 :V 乙酸乙酯 =3:1) A yellow solid was obtained, which was confirmed to be benzofuran-pyrrole derivative 3a by NMR a...

Embodiment 2

[0034] Replace 2a in Example 1 with 2b, and other conditions are the same as Example 1, and its yield is 86%.

[0035]

[0036] Spectrum analysis data 3b:

[0037] Yellow solid, melting point 249-250°C; 1 H-NMR (400MHz, CDCl 3 )δ10.32(s,1H),7.82(d,J=8.4Hz,2H),7.66(t,J=7.6Hz,2H),7.47(d,J=3.2Hz,2H),7.33-7.29( m, 2H), 7.11(s, 1H), 6.98(d, J=8.8Hz, 2H), 3.90-3.87(m, 7H), 3.78-3.76(m, 4H) (Figure 3); 13 C-NMR (CDCl 3 ( Figure 4 ); HRMS(ESI-TOF)m / zcalculated for C 25 h 23 N 2 o 5 [M+H] + :431.1596 found: 431.1607.

Embodiment 3

[0039] Replace 2a in example 1 with 2c, other conditions are the same as example 1, and its yield is 77%.

[0040]

[0041]Spectral analysis data 3c:

[0042] Yellow solid, melting point 264-266°C; 1 H-NMR (400MHz, CDCl 3 )δ10.54(s,1H),7.83(d,J=8.4Hz,2H),7.68-7.65(m,2H),7.50-7.49(d,J=2.4Hz,1H),7.33-7.29(m , 2H),7.20(s,1H),6.98(d,J=8.8Hz,2H),3.87(s,3H),3.83(t,J=6.8Hz,2H),3.70 (t,J=6.8Hz ,2H),2.11-2.04(m,2H),1.97-1.91(m,2H)( Figure 5 ); 13 C-NMR (CDCl 3 , 100MHz) δ190.2,160.3,159.8,157.7,155.2,131.5,129.4,127.4,127.3,126.7, 126.4,124.6,122.9,122.8,114.3,114.1,113.1,100.3,55.6,49.3,48. 6); HRMS (ESI-TOF) m / z calculated for C 25 h 23 N 2 o 4 [M+H] + :415.1652 found: 415.1661.

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Abstract

The invention discloses a method for preparing benzofuran-pyrrole compounds by copper catalysis. The method comprises the following steps: carrying out a stirring and refluxing reaction on 1,6-dialkynyl-3-ol compounds represented by formula (1) and isocyanides represented by formula (2) in an organic solvent system with a metal copper salt as a catalyst, carrying out TLC tracking detection until the reaction is completed, and post-treating the obtained reaction solution to obtain the benzofuran-pyrrole compounds represented by formula (3). The method has the advantages of simplicity in operation, easy availability of raw materials and reagents, mild reaction conditions, green and environmentally-friendly reaction system, and easiness in separation and purification of the product, is suitable for synthesizing various highly-functionalized benzofuran-pyrrole compounds, is particularly suitable for large-scale industrial production, and can realize high-efficiency and high-yield production of the benzofuran-pyrrole compounds.

Description

technical field [0001] The invention belongs to the technical field of fine chemical organic synthesis, and in particular relates to a copper-catalyzed method for preparing benzofuran-pyrrole compounds. Background technique [0002] Pyrrole and benzofuran are two important classes of small organic molecule frameworks. Pyrrole is not only the key structural unit of many bioactive natural products, drugs, and organic conductive materials, but also a multipurpose organic synthon. Therefore, the development of synthetic methods for pyrrole rings has always been one of the important research topics in organic synthetic chemistry. [0003] The methods that have been developed include: Knorr synthesis, Hantzsch reaction, Paal-Knorr condensation reaction, reductive coupling reaction, aza-Wittig reaction, multi-component coupling methodology and other multi-step operations. However, these disclosed catalytic systems still have some defects, such as narrow substrate scope, harsh reac...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D405/06
CPCC07D405/06
Inventor 吕兰兰陈新义刘建全王香善
Owner XUZHOU NORMAL UNIVERSITY
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