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Method for preparing Jue-type derivative

A compound and cyclization reaction technology, which is applied in the preparation of carboxylic acid nitrile, the preparation of carbon-based compounds, chemical instruments and methods, etc., can solve the problems of harsh reaction conditions, limited substrate applicability, and complicated reaction steps. The reaction operation is simple, universal, and the effect of efficient reaction

Active Publication Date: 2015-05-20
TSINGHUA UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The reported synthesis methods often have limited substrate applicability, difficult synthesis of starting materials, sometimes cumbersome reaction steps, and harsh reaction conditions [Selected papers: (1) Clelias, W.et al.J.Org.Chem.1964, 29(11),3373;(2)Lyle,T.et al.J.Org.Chem.1979,44(26),4933;(3)Le Houllier,C.S.et al.J.Org.Chem.1983, 48(10),1682;(4)Hamza,K.et al.Org.Lett.2004,6(6),925;(5)Das,A.et al.J.Org.Chem.2007,72( 24), 9214; (6) Isobe, H. et al. Org. Lett. 2009, 11 (17), 4026; (7) Okamoto, H. et al. Org. Lett. 2011, 13 (10), 2758 ]

Method used

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  • Method for preparing Jue-type derivative
  • Method for preparing Jue-type derivative
  • Method for preparing Jue-type derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Weigh the catalyst CuCl 2 2H 2 O8.5mg (0.05mmol), 220mg (1mmol) of o-acetyltoluene, a compound belonging to formula II, 505mg (5mmol) of base triethylamine, and 2mL of 1,4-dioxane were added to a 50-mL glass with a lid In the reaction tube, then seal the reaction tube, place the reaction tube in an oil bath and heat to 130°C, stir and keep warm for cyclization reaction for 10h, then cool to room temperature to obtain the target product 12-methyl-5-phenyl -6-benzoyl Reaction result: the isolated target product 12-methyl-5-phenyl-6-benzoyl Weigh, calculate the isolated yield of this product to be 64%.

[0025] This embodiment prepares the target product 12-methyl-5-phenyl-6-benzoyl The structure of the confirmation data is as follows:

[0026] White solid; mp208–211°C; 1 H NMR (300MHz, CDCl 3 )δ8.90(d,J=8.5Hz,1H),8.69(s,1H),8.11(d,J=8.2Hz,1H),7.86–7.62(m,4H),7.60–7.31(m,6H ),7.19(dt,J=13.6,6.0Hz,3H),7.11–7.03(m,1H),6.95(t,J=7.5Hz,1H),6.80(d,J=7.5Hz,1H),2.94 (s...

Embodiment 2

[0030] Weigh CuCl respectively 2 2H 2 O8.5mg (0.05mmol), 262mg (1mmol) of 1-p-propylphenyl-2-o-acetylphenylacetylene, 505mg (5mmol) of triethylamine, and 2mL of 1,4-dioxane were added to 50- mL glass reaction tube, then seal the reaction tube, place the reaction tube in an oil bath and heat to 130°C, stir and keep warm for cyclization reaction for 10h and then cool to room temperature to obtain the target product 12-methyl-5- p-Propyl-6-p-propylbenzoyl Reaction result: the separated target product 12-methyl-5-p-propylphenyl-6-p-propylbenzoyl Weigh, calculate the isolated yield of this product to be 54%.

[0031] This embodiment prepares the target product 12-methyl-5-p-propylphenyl-6-p-propylbenzoyl The structure of the confirmation data is as follows:

[0032] White solid; mp157–158°C; 1 H NMR (300MHz, CDCl 3 )δ8.84(d,J=8.5Hz,1H),8.64(s,1H),8.05(d,J=8.1Hz,1H),7.78(dd,J=8.1,5.7Hz,2H),7.67( t,J=7.6Hz,1H),7.51(t,J=7.5Hz,2H),7.44(t,J=7.5Hz,1H),7.33(d,J=8.1Hz,2H),7.18(d...

Embodiment 3

[0036] Weigh CuCl respectively 2 2H 2 O8.5mg (0.05mmol), 238mg (1mmol) of 1-p-fluorophenyl-2-o-acetylphenylacetylene, 505mg (5mmol) of triethylamine, and 2mL of 1,4-dioxane were added to 50- mL glass reaction tube, then seal the reaction tube, place the reaction tube in an oil bath and heat to 130°C, stir and keep warm for cyclization reaction for 10h and then cool to room temperature to obtain the target product 12-methyl-5- p-Fluorophenyl-6-p-fluorobenzoyl Reaction result: the isolated target product 12-methyl-5-p-fluorophenyl-6-p-fluorobenzoyl Weigh, calculate the isolated yield of this product to be 50%.

[0037] This embodiment prepares the target product 12-methyl-5-p-fluorophenyl-6-p-fluorobenzoyl The structure of the confirmation data is as follows:

[0038] white solid; mp228–230℃; 1 H NMR (300MHz, CDCl 3 )δ8.88(d,J=8.5Hz,1H),8.66(s,1H),8.11(d,J=8.2Hz,1H),7.82–7.41(m,8H),7.12(dd,J=11.4 ,4.1Hz,2H),6.86(t,J=8.6Hz,2H),6.79–6.64(m,2H),2.93(s,3H); 13 C NMR (75M...

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Abstract

The invention discloses a method for preparing a Jue-type derivative. The method comprises the following steps: substituting o-acetyl diaryl acetylene by a compound represented by the formula II, uniformly mixing alkaline and a catalyst in a solvent to generate cyclization reaction, and at the end of the reaction, obtaining the compound represented by the structural general formula I. According to the method, the catalyst adopts copper salt. The catalyst is low in cost, safe and readily available; reaction conditions are simple, convenient, green and environment-friendly; the catalyst system represents high efficiency and high selectivity; the method has an important application value.

Description

technical field [0001] The invention belongs to the technical field of catalytic synthesis of fine chemical products, and relates to a preparation methods of class derivatives. Background technique [0002] Derivatives are very important compounds, widely used in cell experiments and OLED blue light materials. Derivatives can be used as inhibitors of some enzymes, so they can be used as drugs to treat diseases caused by these parasites by inhibiting the expression of certain genes or enzyme activities of parasites [Selected papers: Medrano, F.J.et al. J. Med. Chem. 2003, 46(12), 2548]. In addition, due to the formula shown in I The derivatives have good photoelectric properties, so they have great application value in blue light materials. therefore, The new synthetic method of quasi-derivatives has practical application value and has been highly concerned by researchers in related fields. [0003] There are many active sites in the skeleton of quasi-compounds,...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C49/788C07C49/813C07C49/84C07C45/74C07C255/56C07C253/30C07D333/22C07B37/10
CPCC07B37/10C07C45/74C07C253/30C07D333/22C07C49/788C07C49/813C07C49/84C07C255/56
Inventor 华瑞茂郭彪
Owner TSINGHUA UNIV