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2,3-Disubstituted indoline derivatives and preparation method thereof

An indoline, disubstituted technology, applied in the field of 2,3-disubstituted indoline derivatives and their preparation, can solve the problems of expensive reagents, harsh reaction conditions and the like, and achieve the effect of increasing diversity

Inactive Publication Date: 2016-08-17
CHINA AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these synthetic methods usually need to form indole or indoline skeletons through multi-step reactions, and there are problems such as relatively harsh reaction conditions and relatively expensive reaction reagents. Therefore, the development of new simple and practical methods for synthesizing indoline derivatives still remains is a research hotspot

Method used

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  • 2,3-Disubstituted indoline derivatives and preparation method thereof
  • 2,3-Disubstituted indoline derivatives and preparation method thereof
  • 2,3-Disubstituted indoline derivatives and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023]

[0024] Put 0.0754g (0.200mmol) of compound 1a, 3mL of dichloromethane and 21ul (0.300mmol) of ethyl butadienoate 2 into a dry 15mL Shrek tube, add 10.5mg (0.040mmol) of triphenylphosphine, acidic Add benzoic acid and mix well for cycloaddition reaction. In this reaction system, the molar ratio of compounds 1a and 2 is 1:1.5, and the molar percentage of compound 1a is 100%. Stir at 25° C. for 48 hours, and use a rotary evaporator to concentrate the reaction solution and pass it through a column (ethyl acetate: ethyl acetate: Petroleum ether=1:5, v / v) to obtain 7.9 mg of 2,3-disubstituted indoline 3a, yield 8%. From the NMR data listed below, the structure of the obtained product is correct.

[0025] NMR data for 3a:

[0026] 1 H NMR (300MHz, CDCl 3 )δ7.8(d,J=8.1Hz,1H),7.8-7.7(m,3H),7.6-7.5(m,3H),7.4-7.3(m,2H),7.2-7.0(m,5H) ,6.3(dd,J=15.5,1.7Hz,1H),4.6(m,1H),4.2(q,J=7.1Hz,2H),3.4(m,1H),2.8(dd,J=18.7,4.0 Hz, 1H), 2.3 (s, 3H), 1.8 (dd, J=18.7, 10.5 Hz, 1H), 1.3 (...

Embodiment 2

[0029]

[0030] Put 0.0754g (0.200mmol) of compound 1a, 3mL of dichloromethane and 21ul (0.300mmol) of ethyl butadienoate 2 into a dry 15mL Shrek tube, add 40ul (0.040mmol) of trimethylphosphine (1M of tetrahydrofuran solution), acid additive benzoic acid, and mix well for cycloaddition reaction. In this reaction system, the molar ratio of compounds 1a and 2 is 1:2.5, and the molar percentage of compound 1a is 100%, stirring at 25° C. for 48 hours, and concentrating the reaction solution with a rotary evaporator and passing through a column (ethyl acetate: ethyl acetate: Petroleum ether=1:5, v / v) to obtain 34.2 mg of 2,3-disubstituted indoline 3a, yield 35%.

Embodiment 3

[0032]

[0033] Put 0.0754g (0.200mmol) compound 1a, 3mL tetrahydrofuran and 21ul (0.300mmol) ethyl butadienoate 2 into a dry 15mL Shrek tube, add 17ul (0.060mmol) tributylphosphine, 4.88mg (0.040 mmol) acid additive benzoic acid, mix well to carry out cycloaddition reaction. In this reaction system, the molar ratio of compounds 1a and 2 is 1:2, and the molar percentage of compound 1a is 100%. Stir at 40° C. for 24 hours, and use a rotary evaporator to concentrate the reaction solution and pass it through a column (ethyl acetate: ethyl acetate: Petroleum ether=1:5, v / v) to obtain 69.4 mg of 2,3-disubstituted indoline 3a with a yield of 71%.

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Abstract

The invention discloses a 2,3-disubstituted indoline derivative and a preparation method thereof. The reaction formula and the reaction condition of the preparation method are shown in the specification. In reactants and products, R1 represents any one of alkyl, alkoxy, a halogen atom and nitryl of which the total number of hydrogen atoms and carbon atoms is 1 to 10; R2 represents any one of the alkyl, the alkoxy, the halogen atom and the nitryl of which the total number of hydrogen atoms and carbon atoms is 1 to 10. According to the preparation method disclosed by the invention, raw materials used are cheap in price and easy to get; a cycloaddition way is adopted and organic phosphine is used as a catalyst for reaction which belongs to atom economic reaction; no transition metal is used as the catalyst, so the product is free of heavy metal residues; a simple and feasible new method is provided for synthesizing the 2,3-disubstituted indoline derivative.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and relates to a new class of 2,3-disubstituted indoline derivatives with various structures and a preparation method thereof. Background technique [0002] Indole, indoline and their derivatives are the structural units of a variety of natural products and drugs with important biological activities, with diverse biological activities such as anticancer, antibacterial, antiviral, and anti-infection (Drug Dev.Res.2009 , 70, 145–168; J.Am.Chem.Soc.2013, 135, 6442-6445); in the agricultural field, indole compounds can be used as growth regulators; some compounds containing indole structural units also have herbicidal activity ( CN 101903393 B[P]; CN 102317275A[P]); Indoline spiro compounds can be used as pesticides (US 058 897[p].2005; US 7105482[P].2006). Among them, functionalized 2,3-substituted indoline derivatives have also attracted much attention. As a class of biologically active structural...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/26
CPCC07D209/26
Inventor 肖玉梅郭红超高阵阵王昌袁春浩周磊杰
Owner CHINA AGRI UNIV
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