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Method for preparing 5-sulfonyl methyl oxazole derivative

A technology for sulfonylmethyloxazole and its derivatives, which is applied in the field of preparing 5-sulfonylmethyloxazole derivatives, can solve problems such as lack of preparation methods, and achieve the effects of environmental friendliness, simple reaction operation, and high yield

Inactive Publication Date: 2015-04-29
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, this type of compound lacks ready-made preparation methods (Document 3: Sakamoto, K.; Kondo, Y.; Suginome, T.; Ohba, S.; Yamanaka, H.Synthesis1992, 552)

Method used

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  • Method for preparing 5-sulfonyl methyl oxazole derivative
  • Method for preparing 5-sulfonyl methyl oxazole derivative
  • Method for preparing 5-sulfonyl methyl oxazole derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024]

[0025] The reaction was carried out in a reactor. In the air, 0.2 mmol (93 mg) of propargyl amide 1a and DBU (10 mol%, 3 mg) were added to 2 mL of acetonitrile, and the reaction was stirred at room temperature for 7 hours. After the reaction was finished, the solvent was removed under vacuum, and then the sample was dissolved in dichloromethane and loaded for silica gel column chromatography. The eluent was a mixed solvent of sherwood oil: ethyl acetate=20:1 to obtain 91mg of oxazole 2a. The isolated yield was 98%.

[0026] The characterization data of compound 1a are as follows:

[0027] N-(1,3-diphenylprop-2-ynyl)-N-tosylbenzamide(1a).White solid,52%yield,mp139–140C; 1 H NMR (400MHz, CDCl 3 )δ7.75(d,J=7.8Hz,2H),7.53(d,J=6.7Hz,2H),7.38(dd,J=29.1,10.9Hz,8H),7.28–7.13(m,7H), 6.53(s,1H),2.30(s,3H).; 13 C NMR (100MHz, CDCl 3 )δ171.1, 144.8, 136.1, 136.0, 135.1, 131.8, 131.7, 129.3, 128.8, 128.4, 128.2, 127.9, 122.3, 87.4, 84.7, 54.4, 21.5; HRMS (ESI-TOF) m / z: Ca...

Embodiment 2

[0031]

[0032] The reaction was carried out in a reactor, and 0.2 mmol (81 mg) of propargyl amide 1b and DBU (10 mol%, 3 mg) were added to 2 mL of acetonitrile in the air, and the reaction was stirred at room temperature for 7 hours. After the reaction was finished, the solvent was removed under vacuum, and then the sample was dissolved in dichloromethane and loaded for silica gel column chromatography. The eluent was petroleum ether: a mixed solvent of ethyl acetate=20:1 to obtain 72mg of oxazole 2b. The isolated yield was 89%.

[0033] The characterization data of compound 1b are as follows:

[0034] N-(1,3-Diphenylprop-2-ynyl)-N-tosylacetamide(1b).White crystal,55%yield,mp146-147C; 1 H NMR (500MHz, CDCl 3 )δ7.98(d,J=8.4Hz,2H),7.70(dd,J=8.4,1.0Hz,2H),7.48–7.30(m,10H),7.04(s,1H),2.44(s,3H ),2.12(s,3H); 13 C NMR (126MHz, CDCl 3)δ170.2, 145.0, 137.0, 136.8, 131.9, 129.8, 129.1, 128.9, 128.6, 128.4, 128.3, 127.0, 122.2, 87.5, 84.7, 52.5, 25.7, 21.8; HRMS (ESI-TOF) m / z:...

Embodiment 3

[0038]

[0039] The reaction was carried out in a reactor. In the air, 0.2 mmol (65 mg) of propargyl amide 1c and DBU (10 mol%, 3 mg) were added to 2 mL of acetonitrile, and the reaction was stirred at room temperature for 7 hours. After the reaction was finished, the solvent was removed under vacuum, and then the sample was dissolved in dichloromethane and loaded for silica gel column chromatography. The eluent was petroleum ether: a mixed solvent of ethyl acetate=20:1 to obtain 53mg of oxazole 2c. The isolated yield was 81%.

[0040] The characterization data of compound 1c are as follows:

[0041] N-(1,3-Diphenylprop-2-ynyl)-N-(methylsulfonyl)acetamide(1c).White solid,21%yield,mp102-103C; 1 H NMR (500MHz, CDCl 3 )δ7.68–7.62(m,2H),7.54(dt,J=4.0,2.3Hz,2H),7.46–7.33(m,6H),6.90(s,1H),3.45(s,3H),2.23 (s,3H); 13 C NMR (126MHz, CDCl 3 )δ171.9, 136.7, 132.0, 129.3, 129.0, 128.6, 128.4, 126.8, 121.7, 87.8, 84.1, 51.6, 43.0, 25.7; HRMS (ESI-TOF) m / z: Calcd for C 18 h 17 NO...

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Abstract

The invention relates to a method for preparing a 5-sulfonyl methyl oxazole derivative from N-sulfonyl propargyl amide under simple and mild conditions, particularly to a method for almost quantitatively producing the 5-sulfonyl methyl oxazole derivative from substituting N-sulfonyl propargyl amide under the catalysis of a 10 mol% organic base only. Tri-substituted oxazole can be synthesized with the method under the mild conditions. No matter whether the substituent group is an alkyl group or an aryl group, an electron-withdrawing group or an electron-donating group can be well compatible with the reaction.

Description

technical field [0001] The invention relates to a method for preparing 5-sulfonylmethyloxazole derivatives from N-sulfonyl propargyl amide derivatives. Background technique [0002] Oxazoles are a class of important heterocycles, which widely exist in natural products and molecules with physiological activity as important structural units (Document 1: (a) Yeh, V.S.C. Tetrahedron 2004, 60, 11995. (b) Jin, Z .Nat.Prod.Rep.2006,23,464.(c)Wipf,P.Chem.Rev.1995,95,2115.). 5-sulfonylmethyloxazole has been known to selectively inhibit a specific biological link of arthropod insects, and may be used to make the next generation of environmentally friendly insecticides (Document 2: Kumamoto, K.; Miyazaki, H. .Int.Appl.WO2009028727A1, 2009.). However, such compounds lack ready-made preparation methods (Reference 3: Sakamoto, K.; Kondo, Y.; Suginome, T.; Ohba, S.; Yamanaka, H. Synthesis 1992, 552). This synthesis patent provides a convenient and quick method for synthesizing 5-sulfony...

Claims

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Application Information

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IPC IPC(8): C07D263/32A01P7/04A01P7/02
CPCC07D263/32A01N43/76
Inventor 万伯顺于新章李兴伟吴凡
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI