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A kind of arylation method of indoline

A technology of indoline aryl and indoline, which is applied in the field of arylation of indoline, can solve the problems of long synthetic route, harsh conditions, and difficulty in meeting high throughput, and achieve green reaction conditions and simple operation Effect

Active Publication Date: 2022-04-26
SHAOXING UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The disadvantages of these methods are that the synthetic route is long, the yield is low, and the conditions are harsh. It is difficult to quickly obtain indoline derivatives with diverse structures, and it is difficult to meet the needs of high-throughput screening for indolines with diverse structures.

Method used

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  • A kind of arylation method of indoline
  • A kind of arylation method of indoline
  • A kind of arylation method of indoline

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] In a 20mL reaction tube, add magneton, 1-benzyl-indoline (1mmol), terephthalonitrile (0.5mmol), Cs 2 CO 3 (1mmol), N,N-dimethylacetamide (5mL), react at room temperature under 2*427nm blue LED irradiation for 40 hours. The reaction solution was extracted with ethyl acetate, rotary evaporated, and separated by column chromatography (EA:PE=1:16), and then the target product was obtained after rotary evaporation to remove the solvent, with a yield of 81%. product by 1 H-NMR and 13 C-NMR detection confirmed that, 1 H-NMR and 13 The C-NMR data are:

[0026] 1 H NMR (400MHz, CDCl 3 )δppm 7.64 (d, J = 8.0Hz, 2H), 7.54 (d, J = 8.0Hz, 2H), 7.31-7.23 (m, 5H), 7.12 (dd, J = 7.2, 7.2Hz, 1H), 7.11 (d, J=7.2Hz, 1H), 6.77(dd, J=7.2, 7.2Hz, 1H), 6.53(d, J=7.6Hz, 1H), 4.71(dd, J=10.0, 9.6Hz, 1H) , 4.40 and 4.02 (AB q, J = 15.6, 15.6Hz, 1H), 3.47 (dd, J = 16.0, 9.6Hz, 1H), 2.98 (dd, J = 15.6, 10.0Hz, 1H).

[0027] 13 C NMR (100MHz, CDCl 3 )δppm 152.1, 148.4, 137.7, 132.6(×2),...

Embodiment 2

[0031] In a 20mL reaction tube, add magneton, 1-(4-methylbenzyl)-indoline (1mmol), terephthalonitrile (0.5mmol), Cs 2 CO 3 (1mmol), N,N-dimethylacetamide (5mL), react at 56°C and 2*427nm blue LED irradiation for 40 hours. The reaction solution was extracted with ethyl acetate, rotary evaporated, and separated by column chromatography (EA:PE=1:16), and then the target product was obtained after rotary evaporation to remove the solvent, with a yield of 49%. product by 1 H-NMR and 13 C-NMR detection confirmed that, 1 H-NMR and 13 The C-NMR data are:

[0032] 1 H NMR (400MHz, CDCl 3 )δppm 7.63 (d, J = 8.4Hz, 2H), 7.53 (d, J = 8.4Hz, 2H), 7.12-7.07 (m, 6H), 6.74 (dd, J = 8.0, 8.0Hz, 1H), 6.52 (d,J=7.6Hz,1H),4.68(dd,J=9.6,9.6Hz,1H),4.36and 3.95(AB q,J=16.0,16.0Hz,2H),3.44(dd,J=15.6, 9.2Hz, 1H), 2.94(dd, J=16.0, 10.0Hz, 1H), 2.33(s, 3H).

[0033] 13 C NMR (100MHz, CDCl 3 )δppm 152.1, 148.5, 136.8, 134.4, 132.5(×2), 129.2(×2), 128.1(×2), 127.9, 127.7(×3), 124.3, 118.8, 118...

Embodiment 3

[0037] In a 20mL reaction tube, add magneton, 1-(3-methylbenzyl)-indoline (1mmol), terephthalonitrile (0.5mmol), Cs 2 CO 3 (1mmol), N,N-dimethylacetamide (5mL), react at room temperature under 2*427nm blue LED irradiation for 40 hours. The reaction solution was extracted with ethyl acetate, rotary evaporated, and separated by column chromatography (EA:PE=1:16), and then the target product was obtained after rotary evaporation to remove the solvent, with a yield of 76%. product by 1 H-NMR and 13 C-NMR detection confirmed that, 1 H-NMR and 13 The C-NMR data are:

[0038] 1 H NMR (400MHz, CDCl 3 )δ7.68(d, J=8.4Hz, 2H), 7.58(d, J=8.4Hz, 2H), 7.23(dd, J=7.6, 7.6Hz, 1H), 7.16-7.09(m, 4H), 7.07(s,1H),6.80(dd,J=7.2,7.2Hz,1H),6.57(d,J=8.0Hz,1H),4.75(t,J=9.6Hz,1H),4.38and 4.04(AB q,J=15.6,15.6Hz,2H),3.51(dd,J=16.0,9.6Hz,1H),3.02(dd,J=15.6,9.6Hz,1H),2.34(s,3H).

[0039]13 C NMR (100MHz, CDCl 3 )δ152.2, 148.5, 138.2, 137.6, 132.5 (×2), 128.4, 128.4, 128.2, 128.0, 128.0, 127.7 (...

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Abstract

The invention discloses a method for arylation of indoline. The method uses N-substituted indoline and benzonitrile derivatives as raw materials for the first time, uses inorganic base, and stirs for a certain period of time in an organic solvent under illumination conditions, The product was extracted, column chromatographed and rotary evaporated to obtain indoline arylation derivatives. The raw materials used in the method of the invention are simple and easy to obtain, the reaction conditions are green and mild, the operation is simple, no oxidant and metal catalyst are used, and the method has good industrial application value.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to an arylation method of indoline. Background technique [0002] Indole and its derivatives were first obtained by Adolf von Baeyer by reducing isatin in 1866. In 1883, Fescher and Jourdan synthesized indole using pyruvic acid and 1-methylphenylhydrazone, and confirmed its structure the following year. Indoline structure, as a kind of biologically active structural unit, commonly exists in alkaloids and other natural products, such as vinblastine, strychnine, (-)-physostigmine, ajmalinne and so on. Among them, the chiral 2-position substituted and 2,3-position disubstituted indoline derivatives have attracted much attention because of their widespread existence and good biological activity, such as Benzasttain E and angiotensinase inhibitor Pentopril. In addition, indoline as a chiral auxiliary group has also been successfully used in organic asymmetric synthesis. [0003] In re...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/22
CPCC07D209/22
Inventor 冯高峰徐畅沈方旗
Owner SHAOXING UNIVERSITY