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Silicon-containing indoline derivative and preparation method thereof

A technology for silicon-indoline and derivatives, which is applied in the field of silicon-containing indoline derivatives and their preparation, can solve the problems of scarcity of synthesis methods for silicon-containing indoline compounds, and achieve high yield of target products and excellent reaction system Clean, easy-to-handle results

Active Publication Date: 2021-02-12
UNIV OF SCI & TECH OF CHINA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Aiming at the problem that the existing silicon-containing indoline compound synthesis methods are extremely rare, the present invention provides a silicon-containing indoline derivative and a preparation method thereof

Method used

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  • Silicon-containing indoline derivative and preparation method thereof
  • Silicon-containing indoline derivative and preparation method thereof
  • Silicon-containing indoline derivative and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Under nitrogen protection, N,N-disubstituted 2-(2-methyl-propynyl)aniline (R=benzyl, R 1 =H,R 2 =H) 0.2 mmol and 0.4 mmol of azobisisobutyronitrile were added to the Schlenk reaction tube, 2 mL of solvent toluene was added, and 0.3 mmol of tris(trimethylsilyl) silicon was added to seal, and the reaction was carried out at 80° C. The reaction time was: 12 hours; after the reaction was completed, the solvent was removed under reduced pressure, and a white solid was obtained by column chromatography with a yield of 93%.

[0030] 1 H NMR (CDCl 3 ,400MHz),δ(ppm):7.40(dd,J=8.0,1.5Hz,2H),7.30(s,4H),7.27-7.18(m,5H),7.03(t,J=8.1Hz,1H) ,6.93(d,J=7.3Hz,1H),6.71(t,J=7.4Hz,1H),6.39(d,J=7.8Hz,1H),5.76(dd,J=82.6,1.3Hz,2H) ,4.54(d,J=9.6Hz,1H),4.30(d,J=15.8Hz,1H),4.12(d,J=9.6Hz,1H),3.96(d,J=15.7Hz,1H),0.11 (s,27H). 13 C NMR (CDCl 3 ,100MHz),δ(ppm):151.61,148.14,141.47,138.53,134.13,132.00,128.63,128.51,128.49,128.09,127.75,127.70,126.97,124.32,118.21,107.46,78.16,76.84,59.04,51.1...

Embodiment 2

[0032] Under nitrogen protection, N,N-disubstituted 2-(2-methyl-propynyl)aniline (R=methyl, R 1 =H,R 2 =H) 0.2 mmol and 0.4 mmol of azobisisobutyronitrile were added to the Schlenk reaction tube, 2 mL of solvent toluene was added, and 0.3 mmol of tris(trimethylsilyl) silicon was added to seal, and the reaction was carried out at 80° C. The reaction time was: 12 hours; after the reaction was completed, the solvent was removed under reduced pressure, and a white solid was obtained by column chromatography with a yield of 94%. 1 H NMR (400MHz, CDCl 3 ),δ(ppm): 7.41(d,J=6.6Hz,2H),7.32(s,3H),7.13(t,J=7.2Hz,1H),5.89(d,J=0.9Hz,1H), 5.65(d,J=1.6Hz,1H),4.31(d,J=10.6Hz,1H),4.00(d,J=10.6Hz,1H),2.59(s,3H),0.10(s,27H). 13 C NMR (100MHz, CDCl 3 ),δ(ppm): 152.35,147.22,141.46,133.78,132.16,128.59,128.34,127.95,127.91,124.21,118.26,106.91,79.91,59.94,33.97,1.65.

Embodiment 3

[0034]Under nitrogen protection, N,N-disubstituted 2-(2-methyl-propynyl)aniline (R=methyl, R 1 =4-trifluoromethyl, R 2 =H) 0.2 mmol and 0.4 mmol of azobisisobutyronitrile were added to the Schlenk reaction tube, 2 mL of solvent toluene was added, and 0.3 mmol of tris(trimethylsilyl) silicon was added to seal, and the reaction was carried out at 80° C. The reaction time was: 12 hours; after the reaction was completed, the solvent was removed under reduced pressure, and a white solid was obtained by column chromatography with a yield of 97%.

[0035] 1 H NMR (400MHz, CDCl 3 ),δ(ppm): 7.57(dd,J=20.6,8.3Hz,4H),7.15(tt,J=12.0,4.0Hz,1H),6.90(d,J=7.3Hz,1H),6.74(td , J=7.4, 0.9Hz, 1H), 6.54 (d, J=7.8Hz, 1H), 5.79 (dd, J=93.5, 1.5Hz, 2H), 4.37 (d, J=10.8Hz, 1H), 3.96 (d,J=10.8Hz,1H),2.60(s,3H),0.10(d,J=3.1Hz,27H). 19 F NMR (376MHz, CDCl 3 ):-62.53(s). 13 C NMR (100MHz, CDCl 3 ), δ(ppm): 152.14, 146.82, 145.84, 133.37, 132.43, 130.30 (q, J C-F = 30Hz), 128.59, 128.08, 127.14 (q...

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Abstract

The invention discloses a silicon-containing indoline derivative and a preparation method thereof, wherein the structural general formula of the silicon-containing indoline derivative is shown as thefollowing formula I, and in the formula I, R is methyl, benzyl, phenyl, n-amyl, cyclobutyl or cyclopropylmethyl, when R is methyl and R2 is H, R1 is selected from one of fluorine, trifluoromethyl, cyano, tert-butyl, methyl and methyl formate, and when R is benzyl and R1 is H, R2 is selected from one of methyl, trifluoromethyl, methyl formate and fluorine. According to the invention, N,N-disubstituted 2-(2-methyl-propynyl) aniline and tris (trimethylsilyl) silicon are used as raw materials, and are subjected to intramolecular cyclization under the action of an initiator azodiisobutyronitrile toobtain a 3-(1-tri (trimethylsilyl)vinyl) indoline derivative with high yield; and the synthesis of the 3-(1-tri (trimethylsilyl)vinyl) indoline derivative is realized for the first time, the reactionis novel, and the method is of great significance to the development of indoline compounds.

Description

technical field [0001] The invention belongs to the field of organic synthesis, in particular to a silicon-containing indoline derivative and a preparation method thereof. Background technique [0002] Indoline, also known as benzopyrrolidine (or 2,3-indoline), is an aromatic heterocyclic compound whose skeleton structure widely exists in natural products and drug molecules. It is widely used in medicines, such as ajmaline (+)-ajmaline for antiarrhythmic, benzastatin (+)-benzastatinE for protecting nerve cell activity, strchnine for preventing and treating cerebral ischemia, and Blood pressure pentopril pentopril and so on. In addition, indolines are also important intermediates in organic synthesis, and indolin derivatives are also important intermediates for many plant growth regulators in agriculture. However, compared with indoles and indolinones with similar structures, the construction of indoline derivatives is more difficult, the synthesis is also more challenging,...

Claims

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Application Information

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IPC IPC(8): C07F7/08
CPCC07F7/0812
Inventor 汪义丰郑皖欣张凤莲
Owner UNIV OF SCI & TECH OF CHINA