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Benzofuran or naphthofuran derivative and preparation method thereof

A technology of furan derivatives and benzofuran, which is applied in the field of benzofuran or naphthofuran derivatives and their preparation, can solve the problems of long route, high catalyst price, limited expansion of substituted functional groups, etc., and achieve fast reaction speed and Mild conditions and environmentally friendly effects

Inactive Publication Date: 2013-07-24
SHANGHAI UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Traditional methods have played an important role in the synthesis of biologically active benzofurans, but the general route is too long, the requirements for substrates and reaction conditions are too high, and the expansion of substituted functional groups is limited.
Through metal transfer catalysis, although the synthesis method is efficient and common, the environment of the reaction system is relatively harsh, and the price of the catalyst consumed is relatively high.

Method used

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  • Benzofuran or naphthofuran derivative and preparation method thereof
  • Benzofuran or naphthofuran derivative and preparation method thereof
  • Benzofuran or naphthofuran derivative and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Example 1: Iodophenyl diacetate (1.5-2.5 eq), trifluoromethanesulfonic acid (3.5-4.5 eq), benzobis(oxydisiloxane) ( 1 , 1.0 eq), diisopropylamine (3.0~4.0 eq), iodine ylide compound ( 4a , 4.0~5.0 eq), TBAF / THF (3.0~4.0 eq), the obtained benzofuran derivative is: 2-methyl-5,6-oxodisilyl-3-benzofurancarboxylic acid methyl ester ( 5a ), yield 83%, the structure of this compound is:

[0036]

[0037] Molecular formula: C 15 h 20 o 4 Si 2

[0038] Chinese name: Chinese name: 2-Methyl-5,6-oxodisilyl-3-benzofurancarboxylic acid methyl ester

[0039] English name: 2-Methyl-5,6-oxadisilole-3-benzofuran carboxylic acid, methyl ester

[0040] Molecular weight: 320.09

[0041] Appearance: white powder

[0042] H NMR (500 MHz, CDCl 3 ): δ 0.38 (s, 6H), 0.40 (s, 6H), 2.77 (s, 3H), 3.96 (s, 3H), 7.59 (s, 1H), 8.14 (s, 1H) ppm.

[0043] Carbon NMR (125 MHz, CDCl 3 ): δ 1.3, 1.4, 14.7, 51.6, 108.7, 113.1, 124.7, 127.8, 142.4, 143.7, 155.2, 164.3, 165.0 ppm.

[0044]...

Embodiment 2

[0045] Example 2: iodophenyl diacetate (1.5-2.5 eq), trifluoromethanesulfonic acid (3.5-4.5 eq), benzobis(oxydisiloxane) ( 1 , 1.0 eq), diisopropylamine (3.0~4.0 eq), iodine ylide compound ( 4b , 4.0~5.0 eq), TBAF / THF (3.0~4.0 eq), the obtained benzofuran derivative is: ethyl 2-methyl-5,6-oxodisilyl-3-benzofurancarboxylate ( 5b ), yield 91%, the structure of the compound is:

[0046]

[0047] Molecular formula: C 16 h 22 o 4 Si 2

[0048] Chinese name: ethyl 2-methyl-5,6-oxodisilyl-3-benzofurancarboxylate

[0049] English name: 2-Methyl-5,6-oxadisilole-3-benzofuran carboxylic acid, ethyl ester

[0050] Molecular weight: 334.11

[0051] Appearance: white powder

[0052] H NMR (500 MHz, CDCl 3 ): δ 0.39 (s, 6H), 0.40 (s, 6H), 1.45 (t, J = 7.0 Hz, 3H), 2.78 (s, 3H), 4.43 (q, J = 7.0 Hz, 2H), 7.60 (s, 1H), 8.18 (s, 1H) ppm.

[0053] Carbon NMR (125 MHz, CDCl 3 ): δ 1.35, 1.42, 14.6, 14.8, 60.5, 109.0, 113.1, 124.8, 128.0, 142.4, 143.7, 155.2, 164.0, 164.6 pp...

Embodiment 3

[0055] Example 3: Iodophenyl diacetate (1.5-2.5 eq), trifluoromethanesulfonic acid (3.5-4.5 eq), benzobis(oxydisiloxane) ( 1 , 1.0 eq), diisopropylamine (3.0~4.0 eq), iodine ylide compound ( 4c , 4.0~5.0 eq), TBAF / THF (3.0~4.0 eq), the obtained benzofuran derivatives are: 2-methyl-3-acetyl-5,6-oxodisilylbenzofuran ( 5c ), yield 85%, the structure of this compound is:

[0056]

[0057] Molecular formula: C 15 h 20 o 3 Si 2

[0058] Chinese name: 2-methyl-3-acetyl-5,6-oxodisilylbenzofuran

[0059] English name: 2-Methyl-3-acetyl-5,6-oxadisilole benzofuran

[0060] Molecular weight: 304.10

[0061] Appearance: white powder

[0062] H NMR (500 MHz, CDCl 3 ): δ 0.39 (s, 6H), 0.41 (s, 6H), 2.66 (s, 3H), 2.79 (s, 3H), 7.62 (s, 1H), 8.17 (s, 1H) ppm.

[0063] .Carbon NMR (125 MHz, CDCl 3 ): δ 1.3, 1.5, 15.7, 31.4, 113.3, 117.6, 124.5, 127.8, 142.8, 144.0, 155.1, 163.3, 194.3 ppm.

[0064]

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Abstract

The invention relates to a benzofuran or naphthofuran derivative and a preparation method thereof. A structural formula of the derivative is shown in the specification, wherein R1 is OCH3, OC2H5 or CH3, and R2 is CH3 or C6 H5, or R1 and R2 are the same and are (CH2)3, CH2C(CH3)2CH2. The reaction is a typical [3+2] cycloaddition, aryne is produced to participate in the reaction to synthesize the benzofuran or naphthofuran derivative, the requirement of the atomic economic reaction can be met, a completely novel through is provided for establishing a skeleton of benzofuran or naphthofuran, the synthesis method of organic heterocyclic compound is enriched, and the research of the synthesis method of the benzofuran or naphthofuran derivative is not reported in any literature.

Description

technical field [0001] The invention relates to a benzofuran or naphthofuran derivative and a preparation method thereof. Background technique [0002] Aromatic heterocycles are an important and common basic skeleton structure in many pharmaceutical intermediates, natural products and organic optoelectronic materials. Therefore, the synthesis of aromatic heterocycles is one of the hotspots of modern organic synthesis methodology. Furan derivatives have strong biological activity and widely exist in natural and non-natural products. 2-Arylbenzofuran derivatives show good biological activity and pharmacological activity, including anticancer activity, anti-rheumatic activity, anti-filtering pathogen activity, antifungal activity, immunosuppressive activity, anti- Platelet activity, insecticidal activity, anti-inflammatory activity, antifeedant activity, cancer prevention activity. These compounds also have calcium-preventing polymerization activity [ and stimulate plant...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F7/08C07D307/92C07D307/77
Inventor 陈雅丽徐迪张亚娟张杰郑晓杏
Owner SHANGHAI UNIV
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