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A kind of synthetic method of pyrrole carboxylate compound

A technology of ester compound and pyrrole carboxylic acid, which is applied in the direction of organic chemistry, can solve the problems of poor reaction regioselectivity, difficult to obtain substrate, long synthetic route, etc., and achieve the effect of simple operation, wide application range and mild reaction conditions

Active Publication Date: 2021-08-06
HENAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It should be pointed out that although pyrrole carboxylate compounds have important research and application value, the effective methods for the synthesis of such compounds are very limited, and these methods often have the disadvantages of difficult access to substrates, long synthetic routes, and limited reaction areas. Inadequacies such as poor selectivity and cumbersome operation

Method used

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  • A kind of synthetic method of pyrrole carboxylate compound
  • A kind of synthetic method of pyrrole carboxylate compound
  • A kind of synthetic method of pyrrole carboxylate compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022]

[0023] 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%). 2a (0.3mmol, 81mg), PdCl 2 (0.03mmol, 5.3mg), copper acetate (0.3mmol, 54mg) and potassium iodide (0.3mmol, 50mg) were placed in a 10mL Shrek tube, evacuated and filled with CO, and then ethanol (3mmol, 175μL) and acetonitrile (3mL) Add it to the system, raise the temperature to 80°C, and react for 12h. The reaction system was post-treated to obtain the target product 3a (45 mg, 70%). The charac...

Embodiment 2

[0025] 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

[0027] 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.

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Abstract

The invention discloses a method for synthesizing pyrrole carboxylate compounds, belonging to the technical field of organic synthesis. Add N-substituted piperidine 1 into the solvent, and in the presence of copper acetate, 4-dimethylaminopyridine and additives, heat the reaction in oxygen to obtain iodopyrrole compound 2, then compound 2, palladium salt, oxidizing agent, additive Mix with alcohol, and heat reaction in CO atmosphere to obtain pyrrole carboxylate compound 3. The method synthesizes iodopyrroles through a series of cascaded reactions including oxidative ring shrinkage, decarbonylation, dehydrogenation, β-position iodination, and aromatization of N-substituted piperidines, followed by carbonyl insertion with CO and alcohols. reaction to obtain pyrrole carboxylate compounds, which have the advantages of simple raw materials, easy operation, mild conditions, and wide application range of substrates, and provide an economical, practical and green and environmentally friendly new method for the synthesis of pyrrole carboxylate compounds.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a synthesis method of pyrrole carboxylate compounds. Background technique [0002] Pyrrole is an important nitrogen-containing five-membered heterocyclic ring. This structural unit exists in a variety of natural products (such as chlorophyll, heme, and pigments, etc.) and clinical drugs (such as Lipitor for the treatment and prevention of coronary heart disease, etc.) Among them, it is one of the advantageous structural units in the development of new drugs. Therefore, new synthesis methods of pyrrole compounds are important research contents in the fields of synthetic chemistry, medicinal chemistry and biochemistry. [0003] On the other hand, ester group is one of the most important organic functional groups with diverse reactivity. For example, starting from an ester group, new structural units such as methylene, alcohol, aldehyde, ketone, amide, and ac...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D207/34
CPCC07D207/34
Inventor 张新迎王芳范学森何艳
Owner HENAN NORMAL UNIV
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