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A method for jointly constructing 2,4 diaryl oxazoles by acetophenone compounds, ammonium persulfate and dimethyl sulfoxide

A technology of diaryloxazole and dimethyl sulfoxide, which is applied in the field of synthesis of pharmaceutical intermediates, can solve the problems of low yield, difficult to obtain, and high raw material cost, and achieve simple operation, high raw material utilization rate, and low cost Effect

Active Publication Date: 2020-04-21
YUANJIANG HUALONG CATALYST TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The existing oxazole ring construction method has defects such as high raw material cost, low yield, need to use heavy metal or noble metal as a catalyst, and difficulty in obtaining 2,4 disubstituted oxazole, etc. The purpose of the present invention is to provide a method using Cheap acetophenone compounds, quaternary ammonium salts, and dimethyl sulfoxide were used as raw materials to synthesize 2,4-diaryl oxazoles in high yields by a one-pot method under mild reaction conditions and without heavy gold or noble metal catalysis compound-like approach

Method used

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  • A method for jointly constructing 2,4 diaryl oxazoles by acetophenone compounds, ammonium persulfate and dimethyl sulfoxide
  • A method for jointly constructing 2,4 diaryl oxazoles by acetophenone compounds, ammonium persulfate and dimethyl sulfoxide
  • A method for jointly constructing 2,4 diaryl oxazoles by acetophenone compounds, ammonium persulfate and dimethyl sulfoxide

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Experimental program
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Effect test

Embodiment 1

[0071]

[0072] 52.9 mg, 85% yield, dark yellow solid.

[0073] 1 H NMR (400MHz, CDCl 3 )δ8.60(d, J=7.7Hz, 2H), 8.15(s, 1H), 7.85(d, J=7.5 Hz, 2H), 7.68(t, J=7.3Hz, 1H), 7.56(d, J=15.1Hz, 2H), 7.46(d, J=7.5Hz, 2H), 7.39(t, J=7.2Hz, 1H).

[0074] 13 C NMR (101MHz, CDCl 3 )δ178.71, 157.52, 142.68, 136.22, 134.94, 134.03,

[0075] 131.03, 129.91, 128.89, 128.86, 128.49, 125.83.

Embodiment 2

[0077]

[0078] 60.9 mg, 88% yield, orange solid.

[0079] 1 H NMR (400MHz, CDCl 3 )δ8.49(d, J=7.6Hz, 2H), 8.08(s, 1H), 7.72(d, J=7.1 Hz, 2H), 7.34(d, J=7.8Hz, 2H), 7.25(d, J=5.3Hz,2H),2.45(s,3H),2.39(s,3H). 13 C NMR (101MHz, CDCl 3 )δ178.40, 157.59, 145.10, 142.64, 138.77, 135.67, 132.49, 131.16, 129.54, 129.22, 127.17, 125.73, 21.81, 21.32.

Embodiment 3

[0081]

[0082] 63.5 mg, 82% yield, yellow solid.

[0083] 1 H NMR (400MHz, CDCl 3 )δ8.64(d, J=7.7Hz, 2H), 8.04(s, 1H), 7.77(d, J=7.4 Hz, 2H), 7.00(dd, J=17.3, 7.6Hz, 2H), 3.91( s,3H),3.85(s,3H).

[0084] 13 C NMR (101MHz, CDCl 3 )δ177.11, 164.37, 160.02, 157.67, 142.29, 134.90, 133.56, 127.97, 127.16, 122.70, 114.26, 113.80, 55.52, 55.32.

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Abstract

The invention discloses a method for constructing 2,4-diaryloxazole by acetophenone compound, ammonium persulfate and dimethylsulfoxide jointly. The method includes that the acetophenone compound is subjected to cyclization reaction in DMSO (dimethylsulfoxide) solution which contains ammonium persulfate and TBAI (tetrabutylammonium iodide) to obtain 2,4-diaryloxazole. According to the method, thecheap acetophenone compound, ammonium persulfate, dimethylsulfoxide and the like are used as raw materials for one-pot high-yield synthesis of 2,4-diaryloxazole compounds under mild reaction conditions without heavy metal or precious metal catalytic action, and industrial production is benefited.

Description

technical field [0001] The present invention relates to a method for synthesizing oxazole compounds, in particular to a method for synthesizing 2,4 diaryl oxazoles by jointly constructing an oxazole ring with acetophenone compounds, inorganic quaternary ammonium and dimethyl sulfoxide, It belongs to the field of synthesizing pharmaceutical intermediates. Background technique [0002] Oxazole compounds are a class of compounds based on the oxazole ring, which is a five-membered heterocyclic ring containing N and O. Oxazole compounds are widely found in many pharmacologically active molecules and natural products. A very important organic compound, the current common molecular formula with pharmaceutical activity is as follows: [0003] [0004] In the early days, oxazole compounds mainly relied on physical extraction from natural products, but physical extraction alone could no longer meet the needs of the existing society. A large number of researchers have studied the ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D263/32
CPCC07D263/32
Inventor 郭灿城曹重仲郭欣
Owner YUANJIANG HUALONG CATALYST TECH