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Synthetic method of pyrrole-3-formic acid ester compound

A technology of ester compounds and synthesis methods, which is applied in the field of synthesis of pyrrole-3-carboxylate compounds, can solve the problems of complex operation process, harsh reaction conditions, practical limitations, etc., and achieve high atom economy, simple operation, Effect of waste reduction

Inactive Publication Date: 2017-06-13
HENAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although these methods can effectively synthesize pyrrole-3-carboxylate compounds, there are still some problems that need to be solved urgently, such as: catalyst toxicity is large, reaction conditions are harsh, and the operation process is complicated. Practicality is very limited

Method used

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  • Synthetic method of pyrrole-3-formic acid ester compound
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  • Synthetic method of pyrrole-3-formic acid ester compound

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Effect test

Embodiment 1

[0010]

[0011] Add 1a (0.2 mmol, 46 mg) and dimethyl sulfoxide (DMSO, 2 mL) into a 15 mL pressure tube, and stir the reaction at 80°C for 12 hours in an oxygen atmosphere. Then, 5 mL of saturated sodium chloride solution was added to quench the reaction, extracted with ethyl acetate (5 mL × 3), and the organic phases were combined and dried over anhydrous sodium sulfate. After filtration, spin-drying, and separation on a silica gel column (petroleum ether / ethyl acetate = 20:1), the yellow liquid product 2a (42 mg, 92%) was obtained. The characterization data of this compound are as follows: 1 H NMR (400 MHz, CDCl 3 ) δ 1.32-1.36 (m, 3H), 4.28 (q, J = 7.2 Hz, 2H), 5.07 (s, 2H), 6.64 (d, J = 0.8 Hz, 2H), 7.15 (d, J = 7.2 Hz, 2H), 7.34-7.38 (m, 4H). 13 C NMR (100MHz, CDCl 3 ) δ 14.5, 53.9, 59.7, 110.5, 116.6, 122.1, 126.3, 127.3, 128.1, 128.9, 136.8, 164.9. MS: m / z 230 [M+H] + .

Embodiment 2

[0013] According to the method described in Example 1, 1a (0.2 mmol, 46 mg) and dimethyl sulfoxide (DMSO, 2 mL) were added to a 15 mL pressure-resistant tube, and the reaction was stirred at 80°C for 12 hours in an air atmosphere. Then, 5 mL of saturated sodium chloride solution was added to quench the reaction, extracted with ethyl acetate (5 mL × 3), and the organic phases were combined and dried over anhydrous sodium sulfate. After filtration, spin-drying, and separation on a silica gel column (petroleum ether / ethyl acetate = 20:1), the yellow liquid product 2a (26 mg, 56%) was obtained.

Embodiment 3

[0015] According to the method described in Example 1, 1a (0.2 mmol, 46 mg) and dimethyl sulfoxide (DMSO, 2 mL) were added into a 15 mL pressure-resistant tube, and the reaction was stirred at 60 °C for 12 hours in an oxygen atmosphere. Then, 5 mL of saturated sodium chloride solution was added to quench the reaction, extracted with ethyl acetate (5 mL × 3), and the organic phases were combined and dried over anhydrous sodium sulfate. After filtration, spin-drying, and silica gel column separation (petroleum ether / ethyl acetate = 20:1), the yellow liquid product 2a (19 mg, 42%) was obtained.

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Abstract

The invention discloses a synthetic method of a pyrrole-3-formic acid ester compound and belongs to the field of organic synthesis technology. The main point of the scheme is as follows: according to the synthetic method of the pyrrole-3-formic acid ester compound, a dihydropyrrole-3-formic acid ester compound is dissolved in a solvent, and in the presence of an oxidizing agent, reacts at the temperature of 60-120 DEG C so as to prepare the pyrrole-3-formic acid ester compound. In comparison with the prior art, the invention has the following advantages: (1) by the adoption of one-step reaction, waste emission is decreased and environmental burden is reduced; (2) by using oxygen or air as the oxidizing agent, the condition is green and environment-friendly; (3) the reaction is carried out at the temperature of minus 120 DEG C, condition is mild, and operation is simple; (4) the application range of a substrate is wide; and (5) atom economy of the reaction is high.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a synthesis method of pyrrole-3-carboxylate compounds. Background technique [0002] Pyrrole-3-carboxylate compounds not only have significant biological activity and important medicinal value, but also have wide application in the field of synthetic chemistry as reaction intermediates, so the research on the synthesis methods of this kind of compounds has always been chemist's concern. At present, the methods for synthesizing such compounds mainly include: 1) esterification of pyrrole-3-carboxylic acid; 2) condensation reaction of acrylate and substituted isonitrile compounds; 3) condensation reaction of ester-substituted cyclopropane with acetonitrile, etc. Although these methods can effectively synthesize pyrrole-3-carboxylate compounds, there are still some problems that need to be solved urgently, such as: catalyst toxicity is large, reaction condition...

Claims

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Application Information

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IPC IPC(8): C07D207/34
CPCC07D207/34
Inventor 何艳张新迎王芳范学森
Owner HENAN NORMAL UNIV
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