Indolinospirobenzoxazine compound, and synthesis method and use thereof

A technology of indoline spiro and synthetic methods, applied in chemical instruments and methods, organic chemistry, luminescent materials, etc., to achieve the effect of increasing selectivity and increasing stability

Inactive Publication Date: 2004-01-07
TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

For example, U.S. Patent No. 4,936,995 reports a class of benzindoline spirobenzoxazine compounds, but their color tone is still blue

Method used

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  • Indolinospirobenzoxazine compound, and synthesis method and use thereof
  • Indolinospirobenzoxazine compound, and synthesis method and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Synthesis of 1,3.3-trimethyl-6'-n-butyl, 8'-pyrrolidinyl-indoline[2,3']spirobenzo[1,4]oxazine:

[0037] Under nitrogen protection, according to literature [E.FICHER; SCHMITT, BER, 21,1072 (1888) method preparation 1,2,3,3-tetramethyl-indolenine iodonium salt is dissolved in absolute ethanol solution, Add 5wt% catalyst hexahydropyridine, under reflux conditions, drop 2-nitroso-3-n-butoxy- The dehydrated ethanol solution of 5-tetrahydropyrrolyl-phenol is distilled while being added dropwise, and the rate of addition is equal to the rate of solvent distillation. After the dropwise addition is completed. Continue to reflux for 1-2 hours. The solution was distilled, concentrated, and passed through a silica gel column to obtain the product indole spirobenzoxazine compound. 1 HNMR (CDCl 3 ), δ (ppm): 7.45-6.5 (m, 4H,), 5.66 (s, 1H,), 5.57 (s, 1H, Ar-H), 4.1 (t, 2H, OCH 2 ,), 3.32(t, 4H, CH 2 -N-CH 2 ), 2.8(s, 3H, N-CH 3 )2.0(t,4H,N-CH 2 -), 1.8 (p, 2H, -CH 2 -), 1.5...

Embodiment 2

[0039] Synthesis of 1,3,3-trimethyl-6',8'-dimorpholinoindoline-[2,3'], spirobenzo[1,4]oxazine:

[0040] Under nitrogen protection, according to literature E.FICHER; SCHMITT, BER, 21,1072 (1888) method prepared 1,2,3,3-tetramethyl-indolenine iodide salt was dissolved in dehydrated ethanol solution, added 5wt% catalyst hexahydropyridine, under reflux conditions, add dropwise 2-nitroso-3,5-dimorpholino with 1,2,3,3-tetramethyl-indolenine iodide -The dehydrated ethanol solution of phenol, distill while adding dropwise, and make the rate of addition equal to the rate of solvent distillation. After the dropwise addition is completed. Continue to reflux for 1-2 hours. After concentration, pass through a silica gel column to obtain the indole spirobenzoxazine compound, which is recrystallized in ethanol. 1 H NMR, (CDCl 3 ), δ (ppm): 7.4-6.4 (m,, 4H), 5.85 (s,, 1H), 5.95 (s, 1H), 3.85 (t, O-CH 2 , 8H), 3.6(t-N-CH 2 , 8H), 3.2(s, 3H, N-CH 3 )0.95(s, 6H, CH 3 ) has good photochro...

Embodiment 3

[0043] Synthesis of 1-propenyl-3,3-dimethyl-6',8'-dimorpholinoindoline[2,3']-spirobenzo[1,4]oxazine:

[0044] Under nitrogen protection, according to the document E.FICHER; SCHMITT, BER, 21,1072 (1888) method prepared 1-propenyl-2,3,3-trimethyl-indolenine iodonium salt was dissolved in absolute ethanol In the solution, add 5% catalyst hexahydropyridine, and under reflux conditions, add dropwise 2-nitroso- 3,5-Dimorpholino-phenol absolute ethanol, distill while adding dropwise, and make the dropping rate equal to the distillation rate. After the dropwise addition is completed. Continue to reflux for 1-2 hours. After concentration, pass through a silica gel column to obtain the target compound. MP: 59-60°C 1 HNMR (CDCl 3 ), δ (ppm): 1.33 (s, 6H, CH 3 ), 3.15(t, 8H, N-CH 2 ,), 3.25(t, 2H, N-CH 2 -), 3.82(t, O-CH 2 , 8H,), 5.16 (d, 2H, -CH=CH 2 ,), 5.76 (d, 1H, -CH=CH 2 ), 6.0 (2s, 2H, Ar-H), 6.58-7.46 (m,, 5H,). Has good photochromic properties and stability.

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Abstract

The present invention relates to an indolinospirobenzoxazine compound, its synthesis method and application. Said synthesis method includes the following steps: under the protection of nitrogen gas dissolving I-(R1)-2,3,3-trimethyl-pseudoindole iodine salt in anhydrous ethyl alcohol adding hexahydropyridine whose concentration is 0.5 wt%-10 wt% catalyst quantity, under the condition of refluxing drop-adding anhydrous ethyl alcohol solution of 2-nitroso-phenol derivative or 2-nitroso-3-R3-5-R2-phenol which is identical to 1-(R1)-2,3,3-trimethyl-pseudoindole iodine salt in gram molecular weight, drop-adding while distilling, after drop-addition continuously refluxing, concentrating, making the above-mentioned silicon gel column so as to obtain the invented product which can be used for making photochromic materials.

Description

technical field [0001] The invention belongs to the technical field of preparation and application of indoline spirooxazine photochromic materials, and in particular relates to indoline spirobenzoxazine compounds and their synthesis methods and applications. Background technique [0002] Organic photochromic materials have broad application prospects. Compared with inorganic materials, they have the advantages of fast response, easy processing, and low cost. [0003] Indoline spirooxazine compounds are a class of photosensitive materials with certain application value due to their good fatigue resistance and weather resistance, and have been extensively studied. [0004] Photochromism can be roughly described as follows: <chemistry num="001"> <chem file="02123486_cml001.xml" / > < / chemistry> [0005] Photochromic substance A, here is an indoline spirooxazine compound, in a certain wavelength of light (hv 1 ) under the irradiation,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D498/10C09K11/06
Inventor 孟宪娟明阳福樊美公
Owner TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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