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Chromone derivative and synthesis method thereof

A synthetic method and derivative technology, applied in organic chemistry and other fields, can solve the problems of limited substrates and cumbersome synthesis of raw materials, and achieve the effects of simple post-processing, good yield, and simple synthesis

Inactive Publication Date: 2015-01-07
EAST CHINA NORMAL UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the existing technologies have disadvantages such as the need for noble metal catalysis, high temperature, cumbersome raw material synthesis, and limited substrates.

Method used

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  • Chromone derivative and synthesis method thereof
  • Chromone derivative and synthesis method thereof
  • Chromone derivative and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Example 1: Synthesis of 2-methyl-3-(cis-1-phenyl-2-formyl ethyl) enyl chromone

[0029]

[0030] 1-(2'-bromophenyl)-2-phenylethynyl ketone, ethyl acetoacetate, Cs 2 CO 3 , Fe(ClO 4 ) 3 9H 2 O, N, N-dimethylacetamide, the consumption of raw material is o-bromoacetylenone 1-(2'-bromophenyl)-2-phenylethynyl ketone 0.3mmol, ethyl acetoacetate 0.3mmol, inorganic base ( Cs 2 CO 3 )0.6mmol, solvent 3ml, iron salt (Fe(ClO 4 ) 3 9H 2 O) 0.06mmol, reacted at 100°C for 2 hours to obtain the target product formula (IA), a yellow liquid, and the separation yield was 81%.

[0031] NMR data: 1 H NMR (400MHz, CDCl 3 , Me 4 Si) δ1.02-1.09(m, 3H), 2.13(s, 3H), 3.97-4.03(m, 2H), 6.55(s, 1H), 7.18-7.30(m, 4H), 7.32-7.36(m , 1H), 7.39-7.41(m, 2H), 7.52-7.57(m, 1H), 8.13(d, J=7.2Hz, 1H); 13 C NMR (100.6MHz, CDCl 3 , Me 4 Si): δ13.64, 18.68, 59.95, 117.81, 120.73, 121.28, 123.06, 124.97, 126.35, 126.99, 128.93, 129.88, 133.58, 138.47, 148.55, 156.30, 162.69, 1675.23

[003...

Embodiment 2

[0033] Example 2: Synthesis of 2-methyl-3-(cis-1-4'-chloro-phenyl-2-formyl ethyl) enyl chromone

[0034]

[0035]1-(2'-bromophenyl)-2-(4'-chloro)phenylethynyl ketone, ethyl acetoacetate are selected for o-bromoacetylenone, 1,3-dicarbonyl compound, inorganic base, iron salt and solvent respectively 、Cs 2 CO 3 , Fe(ClO 4 ) 3 9H 2 O, N, N-dimethylacetamide, the amount of raw materials is o-bromoacetylenone 1-(2'-bromophenyl)-2-(4'-chloro)phenylethynyl ketone 0.3mmol, ethyl acetoacetate 0.3mmol, 0.6mmol of inorganic base, 3ml of solvent, and 0.06mmol of iron salt were reacted at 100°C for 3 hours to obtain the target product formula (IB), a yellow liquid, and the separation yield was 72%.

[0036] NMR data: 1 H NMR (400MHz, CDCl 3 , Me 4 Si): δ1.14-1.19(m, 3H), 2.23(s, 3H), 4.05-4.14(m, 2H), 6.61(s, 1H), 7.27-7.32(m, 2H), 7.34-7.39( m, 1H), 7.42-7.46(m, 3H), 7.63-7.67(m, 1H), 8.20(d, J=7.2Hz, 1H); 13 C NMR (100.6MHz, CDCl 3 , Me 4 Si) δ13.57, 18.60, 59.99, 117.78, 1...

Embodiment 3

[0038] Example 3: Synthesis of 2-methyl-3-(cis-1-4'-methyl-phenyl-2-formyl ethyl) enyl chromone

[0039]

[0040] 1-(2'-bromophenyl)-2-(4'-methyl)phenylethynyl ketone, ethyl acetoacetate Esters, Cs 2 CO 3 , Fe(ClO 4 ) 3 9H 2 O, N, N-dimethylacetamide, the amount of raw materials is o-bromoacetylenone 1-(2'-bromophenyl)-2-(4'-methyl)phenylethynyl ketone 0.3mmol, ethyl acetoacetate 0.3mmol of ester, 0.6mmol of inorganic base, 3ml of solvent, and 0.06mmol of iron salt were reacted at 100°C for 3 hours to obtain the target product formula (IC), a yellow liquid, and the separation yield was 75%.

[0041] NMR data: 1 H NMR (400MHz, CDCl 3 , Me 4 Si): δ1.13-1.18(m, 3H), 2.22(s, 3H), 2.32(s, 3H), 4.02-4.14(m, 2H), 6.62(s, 1H), 7.11-7.15(m, 2H), 7.27-7.44(m, 4H), 7.59-7.64(m, 1H), 8.21(d, J=7.6Hz, 1H); 13 C NMR (100.6MHz, CDCl 3 , Me 4 Si): δ13.57, 18.53, 20.76, 59.74, 117.70, 119.50, 121.23, 122.99, 124.81, 126.22, 126.82, 129.58, 133.44, 135.43, 140.11, 148.44, 156.21,...

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Abstract

The invention discloses a chromone derivative represented by a formula (I) and a synthesis method thereof. The chromone derivative represented by the formula (I) is synthesized from an o-bromoalkynone compound and an ethyl acetoacetate compound serving as raw materials in the presence of a catalyst and inorganic alkali. The synthesis method disclosed by the invention has the advantages that the raw materials are simple and easily available, the post-treatment is simple and convenient, the catalyst is inexpensive, the yield is good and the environmental friendliness is achieved and the like.

Description

technical field [0001] The invention belongs to the technical field of organic compounds and synthesis, and relates to iron-catalyzed chromone derivatives and an iron-catalyzed synthesis method thereof. Background technique [0002] Chromone compounds are an important class of organic compounds, which widely exist in many natural and non-natural products, and most of them have strong biological activity. It can be used as an intermediate in organic synthesis and has great value in drug synthesis. Therefore, people have paid a lot of attention to the synthesis research of chromone compounds. At present, there are many reports on the synthesis methods of such compounds, and great progress has been made. For example, under the action of metals, alkalis, nitrogen carbenes and other salts, chromone derivatives can be obtained. For example: Literature (1) Awuah, E.; Capretta, A.Org.Lett.2009, 11, 3210. (2) Yang, Q.; Alper, H.J.Org.Chem.2010, 75, 948. (3) Lokhande , P.D.; Sakat...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/22
CPCC07D311/22
Inventor 李艳忠孙霞朱凯秦正晨孔令凯李艳丽
Owner EAST CHINA NORMAL UNIV
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