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A kind of 3-aminothiophene derivative and its synthetic method

A synthesis method and technology of aminothiophene are applied in the direction of organic chemistry, etc., to achieve the effects of cheap raw materials, simple operation and high yield

Active Publication Date: 2021-06-15
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

The classic Gewald thiophene synthesis: under the action of copper, alkyne reacts with elemental sulfur to prepare (Angew.Chem.1961, 73, 114.), successfully achieved the preparation of thiophene at a lower temperature, but the reaction requires transition metal catalysis to achieve

Method used

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  • A kind of 3-aminothiophene derivative and its synthetic method
  • A kind of 3-aminothiophene derivative and its synthetic method
  • A kind of 3-aminothiophene derivative and its synthetic method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026]

[0027] The specific process is: weigh 2a (90mg, 0.3mmol), 3a (123mg, 0.45mmol), tetramethylammonium bromide (46mg, 0.3mmol), lithium tert-butoxide (48mg, 0.6mmol) in a 25mL Schlenk reaction flask In the air, 5 mL of toluene solvent was added, and the reaction was stirred at 110° C. for 3 hours. After the reaction, the volatile components were removed under reduced pressure, and then separated by silica gel column chromatography (the eluent was petroleum ether (60-90°C) / ethyl acetate, v / v=100:1) to obtain the yellow liquid target Product 1a (92 mg, yield 90%). The target product was confirmed by NMR and high-resolution mass spectrometry.

Embodiment 2

[0029] The reaction steps and operation are the same as in Example 1, except that the solvent is ethanol. The reaction was stopped, and the target product 1a (0 mg, yield 0%) was obtained after post-processing.

[0030] Typical Compound Characterization Data

[0031] 3-Benzylaminothiophene derivative 1a, yellow liquid. 1 H NMR (400MHz, CDCl 3 )δ7.65(m,4H,aromatic CHand NH),7.46(m,8H,aromatic CH),7.34(m,4H,aromatic CH),7.09(s,1H,thienyl CH),4.48(s,2H, CH 2 ). 13 C NMR (100MHz, CDCl 3 )δ144.4,141.8,139.8and 134.5(Cq each),129.2,128.8,128.7,127.9,127.6,127.5,127.4,126.5,125.4and 115.3(aromatic CH),51.2(CH 2 ).C 23 h 19 HRMS theoretical value of NS [M+H] + : 342.1316; Measured value: 342.1317.

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Abstract

The invention discloses a 3-aminothiophene derivative and a synthesis method thereof. Using 1-alkylthio-1-amino-1-ene-3-thiocarbonyl ketone and hydrazone as raw materials, inorganic base as base, phase transfer catalyst as additive, under heating conditions, through intermolecular reaction, one-step construction of 3- Aminothiophene derivatives and the obtained 3-aminothiophene derivatives are widely used in the fields of medicine and chemical industry. The method has easy-to-obtain raw materials, simple operation, high efficiency, wide substrate adaptability, good stereoselectivity of products, and diverse functional groups.

Description

technical field [0001] The invention relates to a 3-aminothiophene derivative and a synthesis method thereof. 1-Alkylthio-1-amino-1-ene-3-thiocarbonyl ketone reacts with hydrazone under the action of a phase transfer catalyst and an inorganic base to generate 3-aminothiophene derivatives. [0002] Compared with the reported synthesis method of thiophene derivatives, the present invention has easy-to-obtain raw materials, simple operation, mild synthesis reaction conditions, high efficiency, and the product has good functional group diversity. The amine group in the thiophene structure synthesized by the invention can be further functionalized, and can be used as an intermediate in the structure of medicines and chemical products. Background technique [0003] Thiophene derivatives are widely used in the synthesis of medicines, pesticides, dyes, chemical reagents, polymer additives, etc. Antibiotics with thiophene rings have better efficacy than phenyl homologues. Some new...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D333/36
Inventor 柳竹青余正坤
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI