Catalytic synthesized beta-nitropyrrole derivative and synthetic method thereof

A technology of nitropyrrole and nitropyrrole is applied in the field of synthesis of optically pure β-nitropyrrole compounds, can solve the problems of less research on asymmetric alkylation of pyrrole ring and the like, achieves convenient preparation, low price, high yield effect

Inactive Publication Date: 2015-08-19
JINGCHU UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, because pyrrole is relatively unstable in acidic environment, there are few studies on the asymmetric alkylation of pyrrole ring.

Method used

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  • Catalytic synthesized beta-nitropyrrole derivative and synthetic method thereof
  • Catalytic synthesized beta-nitropyrrole derivative and synthetic method thereof
  • Catalytic synthesized beta-nitropyrrole derivative and synthetic method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Example 1: Synthesis of 2-(2-nitro-1-phenylethyl)-1H-pyrrole

[0019] Preparation of a solution of chiral trimetallic Pd / Sm / Pd complex catalyst: To a stirred solution of ligand (4.15 mg, 0.01 mmol) in 0.4 ml THF, solid Pd(OAc) was added in portions at room temperature 2 (2.24 mg, 0.01 mmol), the mixture was stirred for 15min to obtain a yellow suspension, and Sm(OTf) was added in portions 3 (2.99 mg, 0.005 mmol), the yellow suspension immediately turned into a yellow transparent liquid, and the stirring was continued at room temperature for 15 min to obtain a solution of the chiral trimetallic Pd / Sm / Pd complex catalyst.

[0020] Add 1H-pyrrole (0.60 mmol) and 2-nitrostyrene (0.20 mmol) successively to the above catalyst solution, and stir at room temperature for 65 h. After the reaction, the resulting mixture is separated by column chromatography to obtain a pure product, a yellow solid, 1 H NMR (400 MHz, CDCl 3 ): δ 7.84 (bs, 1H), 7.38-7.29 (m, 3H), 7.25-7.23...

Embodiment 2

[0023] Example 2: Synthesis of 2-[1-(4-bromophenyl)-2-nitroethyl]-5-ethyl-1H-pyrrole

[0024] To a stirred solution of ligand (4.15 mg, 0.01 mmol) in 0.4 ml THF, solid Pd(OAc) was added in portions at room temperature 2 (2.24 mg, 0.01 mmol), the mixture was stirred for 15min to obtain a yellow suspension, and Sm(OTf) was added in portions 3 (2.99 mg, 0.005 mmol), the yellow suspension immediately turned into a yellow transparent liquid. Continue to stir at room temperature for 15 min to obtain a catalyst solution, add 2-ethyl-1H-pyrrole (0.60 mmol) and 4-bromo-2-nitrostyrene (0.20 mmol) successively to the solution, and stir at room temperature for 65 h , after the reaction, the resulting mixture was separated by column chromatography to obtain pure product, brown oil (58.0 mg, 90%). 1 H NMR (400 MHz, CDCl 3 ): δ 7.54 (bs, 1H), 7.50 (d, J = 8.0 Hz, 2H), 7.14 (d, J = 8.0 Hz, 2H), 5.96 (t, J = 4.0 Hz, 1H), 5.86 (t, J = 4.0 Hz, 1H), 4.97 (dd, J = 12.0, 4.0 Hz, 1H...

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PUM

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Abstract

The invention relates to a catalytic synthesized beta-nitropyrrole derivative and a synthetic method thereof, a general formula of the catalytic synthesized beta-nitropyrrole derivative is shown as follows. The preparation method comprises the following steps: a solution of a chiral trimetal Pd / Sm / Pd complex catalyst is performed with in-situ preparation in a solvent, a pyrroles compound and a nitro olefines compound are added while stirring, and a mixture is separated by a column chromatography to obtain a pure product which is the beta-nitro pyrroles derivative. The method has the advantage that trimetal complex is taken as a catalyst for synthesizing the beta-nitro pyrroles derivative, and the method has the advantages of convenient preparation, low price, high yield and realization of large-batch synthesis.

Description

Technical field [0001] The present invention involves the synthesis method of optical pure β -nitrifra pyri -type compounds, and especially involves a method of catalyzing the synthetic synthetic pure β -nitro pyrrole derivatives by triple metal matches. Background technique [0002] The asymmetric Fuk torthization reaction is an important type of carbon-carbon bond.Pig Well is an important structural unit of many natural products and drugs.However, due to the relatively instability of pyrolic in acidic environments, there is less research on the asymmetry of pyrone ring.The present invention reports that in an environment without protection, a dex alkylated reaction occurs without protection. Invention content [0003] The purpose of the present invention is to provide a three -dimensional selective catalytic synthesis of a three -dimensional selective catalysis with simple operation, mild response, low cost, and high income. [0004] method. [0005] A kind of optical pure β -...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D207/33
CPCC07D207/33
Inventor 刘娥刘金丽杨成雄
Owner JINGCHU UNIV OF TECH
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