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A kind of 2-(3-isoquinolyl)-propionic acid ethyl ester derivative and its synthetic method

A synthetic method and the technology of ethyl propionate, applied in the field of 2--ethyl propionate derivatives and their synthesis, can solve the problems of no reports, etc., and achieve the effects of simple operation, high yield and mild reaction conditions

Active Publication Date: 2022-06-28
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the reaction of O-acetyl oxime with allenoic acid ester has not been reported yet.

Method used

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  • A kind of 2-(3-isoquinolyl)-propionic acid ethyl ester derivative and its synthetic method
  • A kind of 2-(3-isoquinolyl)-propionic acid ethyl ester derivative and its synthetic method
  • A kind of 2-(3-isoquinolyl)-propionic acid ethyl ester derivative and its synthetic method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028]

[0029] The specific process is: weigh O-acetyl oxime 2a (53 mg, 0.3 mmol) in the glove box, [RhCp*Cl 2 ] 2 (3.7 mg, 0.006 mmol), pivalic acid (6.1 mg, 0.06 mmol), was added to a 25 mL branched tube, and ethyl allenoate 3a (76 mg, 0.6 mmol), 1, was added under nitrogen atmosphere 2-Dichloroethane (3 mL) was reacted at 60 °C for 24 h. After the completion of the reaction, rotary evaporation under reduced pressure was used to remove the solvent, and then silica gel column chromatography (petroleum ether (60-90°C) / ethyl acetate: 20:1, v / v) was used to obtain a colorless liquid product 1a (62 mg, yield). rate 85%). The target product was confirmed by NMR spectroscopy.

Embodiment 2

[0031]

[0032] The reaction steps and operations were the same as those in Example 1, and the difference from Example 1 was that the O-acetyl oxime added in the reaction system was 2b (57 mg, 0.3 mmol). The reaction was stopped, and the target product 1b (68 mg, yield 88%) was obtained as a pale yellow liquid after post-treatment. The target product was confirmed by nuclear magnetic resonance spectroscopy and high-resolution mass spectrometry.

Embodiment 3

[0034]

[0035] The reaction steps and operations were the same as those in Example 1, and the difference from Example 1 was that the O-acetyl oxime added in the reaction system was 2c (62 mg, 0.3 mmol). The reaction was stopped, and the target product 1c (75 mg, yield 92%) was obtained as a pale yellow liquid after post-treatment. The target product was confirmed by nuclear magnetic resonance spectroscopy and high-resolution mass spectrometry.

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PUM

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Abstract

The invention discloses a 2-(3-isoquinolyl)-ethyl propionate derivative and a synthesis method thereof. Using O-acetyl oxime, which is easy to prepare, has structural diversity and multiple reaction centers, as a raw material, under the action of rhodium salt, the ortho-position C–H bond of the aromatic ring in O-acetyl oxime is activated to react with allenoate A series of 2‑(3‑isoquinolinyl)‑ethyl propionate derivatives with different structures were synthesized through the coupling reaction, and the products could be further transformed into functionalized products. The method has easy-to-obtain raw materials, simple operation, mild reaction conditions, and the diversity of functional groups without pre-functionalization.

Description

technical field [0001] The invention relates to a 2-(3-isoquinolinyl)-propionic acid ethyl ester derivative and a synthesis method thereof. Using O-acetyl oxime with easy preparation, structural diversity and multiple reaction centers as raw material, the ortho-position C-H bond of aromatic ring in O-acetyl oxime is activated under the action of rhodium salt, and it is coupled with allenoic acid ester. After the reaction, a series of 2-(3-isoquinolinyl)-propionic acid ethyl ester derivatives with different structures were synthesized. Compared with the existing method for synthesizing isoquinoline derivatives, the present invention has the advantages of easy availability of raw materials, simple operation, mild reaction conditions and environmental friendliness; and no oxidant or reducing agent needs to be added in the reaction, no pre-functionalization is required, and there are atomic economical features. Background technique [0002] Compared with traditional methods, c...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D217/14C07D217/02C07D217/16
CPCC07D217/14C07D217/02C07D217/16
Inventor 余正坤汪全南
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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