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Method for synthesizing coumarin [4,3-d]pyrimidine derivative

A technology for aminocoumarins and compounds is applied in the field of preparing coumarin [4,3-d]pyrimidine derivatives, and can solve the problems of complicated steps, easy moisture absorption of reactants, and difficulty in directly preparing pyrimidine ring target compounds.

Inactive Publication Date: 2019-09-27
CHANGSHA UNIVERSITY OF SCIENCE AND TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] Looking at the literature, the defects in the prior art are: the substrate needs to be highly pre-functionalized, the reaction reagent is greatly excessive, the reactant is easy to absorb moisture, the reaction needs metal catalysis, the steps are cumbersome, and it is difficult to directly prepare the target substance with all-carbon substitution of the pyrimidine ring. and other shortcomings

Method used

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  • Method for synthesizing coumarin [4,3-d]pyrimidine derivative
  • Method for synthesizing coumarin [4,3-d]pyrimidine derivative
  • Method for synthesizing coumarin [4,3-d]pyrimidine derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] 4-aminocoumarin, benzaldehyde, ammonium iodide synthesize 2,4-diphenylcoumarin[4,3-d]pyrimidine (the structural formula of this compound is shown in formula III-1), comprising the following steps:

[0024] Into the reaction tube, add 4-aminocoumarin (0.2mmol), ammonium iodide (0.24mmol), and solid benzaldehyde (0.6mmol) successively, and use a double-row pipe system to pump / fill oxygen and circulate it three times. Inject dimethyl sulfoxide (0.2 mmol, 18 μL) and chlorobenzene (0.5 mL) sequentially through a syringe, seal the tube and react at 150° C. for 24 hours. The reaction system was treated with dichloromethane and water, and the organic phase was evaporated to dryness under reduced pressure. The obtained solid was recrystallized (dichloromethane / ethanol) to obtain the target product, and the calculated separation yield was 95%;

[0025]

[0026] White solid, m.p.243°C. 1 H NMR (400MHz, CDCl 3 )δ8.83(dd,J=7.9,1.5Hz,1H), 8.74(dd,J=8.0,1.7Hz,2H),7.79(dd,J=7.9,1....

Embodiment 2

[0028] For the synthesis of the compound shown in formula III-2, the benzaldehyde in Example 1 was replaced with 2-methylbenzaldehyde, and other reaction conditions were the same as in Example 1, with a yield of 55%;

[0029]

[0030] White solid, m.p.172-173°C. 1 H NMR (400MHz, CDCl 3 )δ8.73(d, J=7.9Hz, 1H), 8.22(d, J=7.2Hz, 1H), 7.68(t, J=7.6Hz, 1H), 7.46–7.25(m, 9H, overlapped with CDCl 3 ),2.79(s,3H),2.25(s,3H). 13 C NMR (100MHz, CDCl 3 )δ172.1,169.5,159.4, 158.0,154.4,138.9,138.7,136.6,134.9,134.3,131.9,131.8,130.9,130.1,129.1,127.7, 126.2,125.9,125.7,124.9,118.3,117.2,110.6,22.3,19.7 .

Embodiment 3

[0032] For the synthesis of the compound shown in formula III-3, the benzaldehyde in Example 1 was replaced with 4-methylbenzaldehyde, and other reaction conditions were the same as in Example 1, with a yield of 91%;

[0033]

[0034] White solid, m.p.259-261°C. 1 H NMR (400MHz, CDCl 3 )δ8.79(d, J=7.9Hz, 1H), 8.61(d, J=8.0Hz, 2H), 7.71(d, J=7.8Hz, 2H), 7.66(t, J=7.8Hz, 1H) ,7.44(t,J=7.6Hz,1H),7.37(d,J=8.3Hz,1H),7.33(d,J=7.9Hz,4H),2.47(s,3H),2.46(s, 3H) . 13 C NMR (100MHz, CDCl 3 )δ171.2, 165.9, 160.2, 158.8, 154.3, 143.0, 140.8, 135.4, 134.0, 133.8, 129.6, 129.54, 129.47, 128.8, 125.8, 124.6, 118.4, 117.0, 109.5, 21.6.7, 2

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Abstract

The invention discloses a method for synthesizing a coumarin [4,3-d]pyrimidine derivative. The method comprises the following step: a 4-aminocoumarin compound, aromatic aldehyde and ammonium iodide react in chlorobenzene under the oxidizing conditions to obtain a target compound. The method of the invention has the advantages of simple steps, low cost, no metal participation, etc., can overcome the disadvantage in the prior art that a substrate needs to be highly pre-functionalized, the amount of the reaction reagent is excessive, the reactants are easy to absorb moisture, the reaction requires metal catalysis, the steps are cumbersome and it is difficult to directly prepare a pyrimidine ring all-carbon-substituted target product, and can play an important role in the research field of coumarinopyrimidine derivatives.

Description

technical field [0001] The present invention relates to a kind of preparation method of coumarin and pyrimidine condensed ring compound, specifically, relate to a kind of preparation method of coumarin [4,3- d] Methods of pyrimidine derivatives. Background technique [0002] Coumarin and pyrimidine nuclei are two very important heterocyclic skeletons of various natural products and bioactive drugs. As the fused-ring derivatives of these two fragments, coumarin[4,3-d]pyrimidine derivatives have been found to have diverse activities, attracting widespread interest from chemists. To date, several synthetic methods for the preparation of such scaffolds have been established. For example, Trimarco et al. reported a two-step synthesis of coumarin [4,3-d] pyrimidine derivatives from 4-azidocoumarin and enamine through an intermediate amidine (Tetrahedron 2005, 61, 4957- 4964), Chaskar etc. reported that choline hydroxide was used as catalyst and solvent to realize the condensati...

Claims

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Application Information

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IPC IPC(8): C07D491/052
CPCC07D491/052
Inventor 李江胜姜思谢欣芸杨盼盼陈晶李志伟欧阳楚豪江湖
Owner CHANGSHA UNIVERSITY OF SCIENCE AND TECHNOLOGY
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