4, 4-disubstituted-4, 5-dihydro-1H-imidazole-5-one and derivatives thereof as well as synthesis method thereof
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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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However, the synthetic methods of such compounds are rarely disclosed, and m
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[0106] Example 12 Synthesis of 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℃ After reacting for 24 hours, 36.8 mg of pure product was obtained by conventional treatment with a yield of 86%.
[0109] The NMR and MS data of the product of Example 1 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.
Example Embodiment
[0111] Example 22-Synthesis of (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%.
Example Embodiment
[0114] The NMR and mass spectrum data of the product of Example 2 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,found229.1333.
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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...
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