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A kind of preparation method of 3,3-disubstituted indolone compounds

A compound, the technology of indolinone, applied in the field of organic photochemical synthesis, can solve the problems of reducing reaction cost, poor economy, high price, etc., and achieve the effect of reducing reaction cost, good application prospect and easy operation

Inactive Publication Date: 2018-07-27
TONGJI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In recent years, with the deepening of the application of visible light catalysis in organic synthesis, the research on the synthesis of similar compounds by visible light catalysis has also been reported. [5] , trifluoromethyl [6] ,alkyl [7] Indolinone compounds have been synthesized, but the indolinone compounds containing malonyl group have not been synthesized by visible light, and the photocatalysts used in these works are metal metal ruthenium (II) and iridium (( III) and other metal complexes are expensive and difficult to handle, so the economy is not good, and we not only synthesized new indolinone compounds, but also used Eosin Y, which is cheap, easy to handle and has no pollution to the environment. Catalyst, which reduces the reaction cost and is environmentally friendly

Method used

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  • A kind of preparation method of 3,3-disubstituted indolone compounds
  • A kind of preparation method of 3,3-disubstituted indolone compounds
  • A kind of preparation method of 3,3-disubstituted indolone compounds

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Experimental program
Comparison scheme
Effect test

Embodiment 1-10

[0034] Reaction equation:

[0035]

[0036] Proceed as follows:

[0037] In the dry reaction tube, add 0.25mmol of N-arylacrylamide compound, 0.5mmol of diethyl bromomalonate, 0.005mmol of Eosin Y, 0.1mmol of triethylamine and 0.5mmol of sodium bicarbonate , And then add 2mL of a mild solution of N,N-dimethylaniline and water, under the 12W blue LED light, react in the air at room temperature for 24h. After the reaction is over, wash with water, extract, and dry again. The organic solvent was removed under reduced pressure, and the product was separated by thin-layer chromatography and column chromatography (petroleum ether / ethyl acetate=25 / 1). The resulting product yield is 85%.

[0038]

[0039] 1 H NMR (400 MHz, CDCl 3 ): δ 7.34–7.26 (m, 1H), 7.19 (d, J = 7.3 Hz,1H), 7.08 (t, J = 7.9 Hz, 1H), 6.87 (d, J = 7.8 Hz, 1H), 4.15 (q, J = 7.1 Hz, 2H), 3.85 (m, J = 10.8, 7.1 Hz, 1H), 3.74–3.63 (m, 1H), 3.24 (s, 3H), 3.04(dd, J = 8.1, 5.5 Hz, 1H), 2.63–2.49 (m, 2H), 1.41 (s, 3H), 1....

Embodiment 2

[0042] Reaction equation

[0043]

[0044] Proceed as follows:

[0045] In the dry reaction tube, add 0.25mmol of N-arylacrylamide compound, 0.5mmol of diethyl bromomalonate, 0.005mmol of Eosin Y, 0.1mmol of triethylamine and 0.5mmol of sodium bicarbonate , And then add 2mL of a mild solution of N,N-dimethylaniline and water, under the 12W blue LED light, react in the air at room temperature for 24h. After the reaction is over, wash with water, extract, and dry again. The organic solvent was removed under reduced pressure, and the product was separated by thin-layer chromatography and column chromatography (petroleum ether / ethyl acetate=25 / 1). The resulting product yield was 86%.

[0046] 1 H NMR (400 MHz, CDCl 3 ): δ 7.10 (d, J = 7.8 Hz, 1H), 7.01 (s, 1H), 6.77 (d, J = 7.9 Hz, 1H), 4.22–4.12 (m, 2H), 3.87 (dq, J = 10.8, 7.1 Hz, 1H), 3.74 (dq, J = 10.8, 7.1 Hz, 1H), 3.23 (s, 3H), 3.06 (dd, J = 8.0, 5.5 Hz,1H), 2.56 (qd, J = 14.3, 6.8 Hz, 2H), 2.36 (s, 3H), 1.41 (s, 3H), 1.25 ...

Embodiment 3

[0049] Reaction equation:

[0050]

[0051] Proceed as follows:

[0052] In the dry reaction tube, add 0.25mmol of N-arylacrylamide compound, 0.5mmol of diethyl bromomalonate, 0.005mmol of Eosin Y, 0.1mmol of triethylamine and 0.5mmol of sodium bicarbonate , And then add 2mL of a mild solution of N,N-dimethylaniline and water, under the 12W blue LED light, react in the air at room temperature for 24h. After the reaction is over, wash with water, extract, and dry again. The organic solvent was removed under reduced pressure, and the product was separated by thin-layer chromatography and column chromatography (petroleum ether / ethyl acetate=25 / 1). The resulting product yield is 90%.

[0053] 1 H NMR (400 MHz, CDCl 3 ): δ 7.13 (d, J = 7.9 Hz, 1H), 7.04 (s, 1H), 6.79 (d, J = 7.9 Hz, 1H), 4.16 (q, J = 7.1 Hz, 2H), 3.88 (dq, J = 10.8, 7.1Hz, 1H), 3.71 (dq, J = 10.8, 7.2 Hz, 1H), 3.24 (d, J = 6.7 Hz, 3H), 3.09 (dd, J = 8.0, 5.5 Hz, 1H), 2.70–2.48 (m, 4H), 1.42 (s, 3H), 1.28–1.22 (m,...

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Abstract

The invention relates to a synthesis method of 3,3-disubstituted indolone compounds. The method comprises the following step: under the irradiation of a 12W, carrying out reaction on substrates N-arylacrylamide compounds and diethyl bromomalonate in room-temperature air for 24 hours by using cheap processable environment-friendly EosinY as a visible light catalyst under the condition of adding triethylamine and an inorganic alkali, thereby preparing a series of malonyl-containing indolone compounds. Compared with the prior art, the method can be used for preparing various malonyl-containing indolone compounds under mild reaction conditions, avoids the use of the metal complex catalyst, and has the characteristics of high economy and environment friendliness.

Description

Technical field [0001] The invention relates to a method for preparing 3,3-disubstituted indolinone compounds under visible light, and belongs to the field of organic photochemical synthesis. The reaction has the characteristics of green, easy operation and high reaction efficiency. Background technique [0002] 3,3-Disubstituted indolinone compounds are important molecular frameworks for many basic natural products and bioactive drugs, and the difference in the type and spatial configuration of the substituents at the 3 substitution position of indolinones makes this type of Substances have different biological activities. Therefore, these compounds are widely used in medicine, organic synthesis, pesticides and other fields [1,2] . [0003] The synthesis of such compounds has also been extensively studied. The most commonly used method in the research is to use transition metal catalyzed N-arylacrylamide to cyclize with free radicals to synthesize five-membered azacyclic indoli...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/34C07D209/60
CPCC07D209/34C07D209/60
Inventor 田文艳张荣华徐松梁中卫孙德立蔡雨国
Owner TONGJI UNIV