Method for preparing iron-catalyzed pyrrole and pyrrole cyclic compounds

A compound, pyrrole technology, which is applied in the field of preparation of pyrrole and pyrrolocyclic compounds, and achieves the effects of low price, green catalytic system, and simple operation

Inactive Publication Date: 2010-08-11
NORTHEAST NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, the reaction of iron-catalyzed ketonylation of 4-pentyne and primary amines to pyrrole and pyrrolocyclic compounds has not been reported in the literature.

Method used

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  • Method for preparing iron-catalyzed pyrrole and pyrrole cyclic compounds
  • Method for preparing iron-catalyzed pyrrole and pyrrole cyclic compounds
  • Method for preparing iron-catalyzed pyrrole and pyrrole cyclic compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] 1) Preparation of 4-pentynone compound 1a

[0025]

[0026] Into a 50 mL round bottom flask equipped with a magnetic stirrer was added anhydrous N,N-dimethylformamide (DMF) (15 mL), N-acetoacetanilide (1.77 g, 10 mmol) and anhydrous potassium carbonate (1.66 g , 12mmol), slowly add 3-bromopropyne (1.43g, 12mmol) dropwise at a room temperature of 20°C under stirring, at a rate of 1 drop / 2 seconds. Stirring was continued for 12 hours to obtain a light yellow reaction liquid. The reaction solution was poured into saturated aqueous sodium chloride solution (20mL), extracted with dichloromethane (3×15mL), and the organic phases were combined, then backwashed with water (3×10mL), dried over anhydrous calcium chloride, Steps such as suction filter, vacuum distillation obtain viscous solid, through silica gel column chromatography (eluent is V 石油醚 :V 乙酸乙酯 =10:3) to obtain 1.25 g of white solid, the structure of the product was confirmed by NMR and MS to be 4-pentynone com...

Embodiment 2

[0033] Replace 4-chloroaniline in "Example 1" with 2-naphthylamine, use benzene as solvent, and the reaction temperature is 50°C. Other conditions are the same as "Example 1". The experimental results are shown in Table 1.

[0034]

[0035] Spectrum analysis data 2b:

[0036] 1 H NMR (500MHz, CDCl 3 )δ=2.04(s, 3H), 2.39(s, 3H), 6.24(s, 1H), 7.07-7.97(m, 13H); 13 CNMR (125MHz, CDCl 3 )δ=12.13, 12.55, 104.10, 114.14, 119.52, 123.21, 125.52, 126.65, 126.74, 127.59, 127.74, 128.64, 128.89, 129.17, 132.51, 133.00, 134.73, 1368.028 -1 ) 3257, 3057, 1638, 1596, 1577, 1498, 1309, 1257, 795, 759, 690;

Embodiment 3

[0038] Replace 4-chloroaniline in "Example 1" with benzylamine, meanwhile, use FeBr 3 , other conditions are the same as "Example 1", and the experimental results are shown in Table 1.

[0039]

[0040] Spectral analysis data 2c:

[0041] 1 H NMR (500MHz, CDCl 3 )δ=2.15(s, 3H), 2.52(s, 3H), 5.05(s, 2H), 6.16(s, 1H), 6.90(d, J=8.0Hz, 2H), 7.06-7.34(m, 5H ), 7.49(s, 1H), 7.59(d, J=8.0Hz, 2H); 13 C NMR (125MHz, CDCl 3 )δ=11.17, 12.21, 46.68, 61.49, 104.32, 113.96, 119.72, 123.39, 125.45, 127.36, 128.20, 128.84, 128.85, 134.54, 136.90, 138.63, 164.09; -1 )3249, 3027, 1638, 1536, 1495, 1435, 1250, 753, 691; MS m / z Calcd: 304.2; Found: 305.2 [(M+1) + ].

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Abstract

The invention belongs to the technical field of organic synthesis chemistry, and particularly relates to a method for preparing iron-catalyzed pyrrole and pyrrole cyclic compounds. The invention provides a method for preparing FeX3-catalyzed pyrrole and thick pyrrole derivatives. The method comprises synthesis of an omega, gamma-alkynone compound, a cyclization reaction and the like. The method develops the cyclization reaction of the FeX3-catalyzed omega, gamma-alkynone compound and a primary amine compound, and can efficiently prepare high-purity pyrrole and pyrrole cyclic compounds with high yield. Compared with the conventional Pd, Au, Ag and Cu catalysts, the FeX3 has the advantages of environment friendliness and low price. The method has the advantages of simple operation, easily obtained raw materials and reagents, mild condition, environment-friendly catalytic system and easy separation and purification of products, is suitable for synthesizing various substituted pyrrole and pyrrole cyclic compounds, and is particularly suitable for large-scale industrial production.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis chemistry, and relates to an iron-catalyzed preparation method of pyrrole and pyrrolocyclic compounds. Background technique [0002] Pyrrole is an important class of heterocyclic compounds. It is not only the key structural unit of many biologically active natural products, drugs, and organic conductive materials, but also a multi-purpose organic synthon. Therefore, the development of synthetic methods for pyrrole rings has always been an important aspect of organic synthetic chemistry. One of the important research topics (Comprehensive Heterocyclic Chemistry III 2008, 3, pp 45-268.; Nat.Prod.Rep., 2006, 23, 517-531.; ARKIVOC2007, 10, 121-141.). The methods that have been developed so far include: Knorr synthesis, Hantzsch reaction, Paal-Knorr condensation reaction, reductive coupling reaction, aza-Wittig reaction, multi-component coupling methodology and other multi-step operations. A...

Claims

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Application Information

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IPC IPC(8): C07D209/08C07D207/34C07D207/333
Inventor 毕锡和王也铭宋金娜廖沛球刘群
Owner NORTHEAST NORMAL UNIVERSITY
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