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4, 4-disubstituted-4, 5-dihydro-1H-imidazole-5-one and derivatives thereof as well as synthesis method thereof

A synthetic method, -1H technology, applied in the direction of organic chemistry, etc., to achieve the effects of excellent chemical properties, reduced environmental pollution, and high atom economy

Active Publication Date: 2014-12-03
XIANGTAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the synthetic methods of such compounds are rarely disclosed, and most of the methods in the published literature require multi-step synthesis.

Method used

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  • 4, 4-disubstituted-4, 5-dihydro-1H-imidazole-5-one and derivatives thereof as well as synthesis method thereof
  • 4, 4-disubstituted-4, 5-dihydro-1H-imidazole-5-one and derivatives thereof as well as synthesis method thereof
  • 4, 4-disubstituted-4, 5-dihydro-1H-imidazole-5-one and derivatives thereof as well as synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0106] Synthesis of Example 12-phenyl-1,3-diazaspiro[4,4]non-1-en-4-one

[0107]

[0108] Take a reaction tube, add 0.9mmol (36mg) sodium hydroxide, 0.2mmol (35.6mg) benzamidine hydrochloride monohydrate, 0.3mmol (31.2μL) cyclohexanone, 0.8mL pyridine under oxygen protection, 80℃ The reaction was carried out for 24 hours, and 36.8 mg of pure product was obtained by conventional treatment, with a yield of 86%.

[0109] The NMR and mass spectrometry data of embodiment 1 product are as follows:

[0110] 1 H NMR (400MHz, CDCl 3 ,ppm)δ10.02(br,1H),7.92(d,J=6.8Hz,2H),7.54-7.49(m,3H),2.07-1.97(m,8H); 13 C NMR (100MHz, DMSO-d 6 , ppm) δ187.8, 157.0, 131.0, 128.2, 127.9, 126.2, 76.9, 36.5, 25.0; MS (EI) m / z (%) 214, 171, 104 (100), 83, 54.

Embodiment 22

[0111] Synthesis of Example 22-(p-methylphenyl)-1,3-diazaspiro[4,4]non-1-en-4-one

[0112]

[0113] Take a reaction tube, add 0.9mmol (36mg) sodium hydroxide, 0.2mmol (34.1mg) 4-methylbenzamidine hydrochloride, 0.3mmol (31.2μL) cyclohexanone, 0.8mL quinoline under oxygen protection, React at 40°C for 48 hours. Conventional treatment yielded 39.7 mg of pure product with a yield of 87%.

Embodiment 2

[0114] The NMR and mass spectrometry data of embodiment 2 product are as follows:

[0115] 1 H NMR (500MHz, CDCl 3 ,ppm)δ10.14(br,1H),7.80(d,J=8.0Hz,2H),7.31(d,J=8.1Hz,2H),2.42(s,3H),2.07-1.94(m,8H ); 13 C NMR (125MHz, DMSO-d 6 , ppm) δ187.3, 156.1, 135.7, 128.3, 128.0, 126.2, 77.0, 36.5, 25.0, 20.5; MS (EI) m / z (%) 228, 185, 118 (100), 83, 65; HRMS calcd.for: C 14 h 17 ON 2 [M+H] + 229.1335, found 229.1333.

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Abstract

The invention relates to a 4, 4-disubstituted-4, 5-dihydro-1H-imidazole-5-one and derivatives thereof as well as a synthesis method thereof. The synthesis method adopts the technical scheme that amidine compounds and ketones are converted into imidazolone and derivatives thereof in the absence of catalysts just under the action of alkali by using air or oxygen as an oxidant and pyridine, quinoline, triethylamine, NMP, DMA, DMSO, 1, 4-dioxane, toluene and the like as an organic solvent. The synthesis method overcomes the difficulties of the existing method for synthesizing imidazolone compounds of complicated synthesis steps, multi-step synthesis processes as well as the use of metal catalysts, metal oxidants or peroxides of chemical equivalent; and 4, 4-disubstituted-4, 5-dihydro-1H-imidazole-5-one and the derivatives thereof are suitably used as multifunctional materials, and are important raw materials especially for producing the medicine Avapro for treating high blood pressure.

Description

technical field [0001] The invention relates to an imidazolone compound and a synthesis method thereof, in particular to a 4,4-disubstituted-4,5-dihydro-1H-imidazol-5-one, a derivative and a synthesis method thereof. Background technique [0002] Imidazolone compounds are widely used and are important raw materials for the manufacture of various functional materials and drugs. Among them, Avapro, a drug for treating hypertension, is a 4,4-disubstituted-4,5-dihydro-1H-imidazole-5- Ketone derivatives. The synthesis methods of such compounds are rarely disclosed, and most of the methods in the published literature require multi-step synthesis. For example J.Heterocyclic Chem., 2010,47,1356-1360; Org.Lett.,2004,6,735-738; Tetrahedron Letters, 2007,48,3109-3113; US6162923 (2000) has reported some synthetic substances Methods. These methods are all completed by a multi-step synthesis process, in which a metal catalyst is required and a stoichiometric metal oxidant or peroxide i...

Claims

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Application Information

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IPC IPC(8): C07D235/02C07D403/04C07D409/04C07D405/04C07D233/70
CPCC07D233/70C07D235/02C07D401/04C07D405/04C07D409/04
Inventor 邓国军谢艳军
Owner XIANGTAN UNIV
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