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Naphthapyran derivative containing sulfonamide groups

A technology of naphthopyran derivatives and alkyl groups, which is applied in the field of naphthopyran derivatives, can solve the problems of difficult large-scale preparation of diphenylnaphthopyran derivatives, and achieve less synthesis steps and photochromic Effects with obvious phenomena and simple synthesis

Active Publication Date: 2011-02-16
SHANGHAI GANTIAN OPTICAL MATERIALS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Since the existing diphenylnaphthopyran derivatives are difficult to prepare on a large scale, the development of novel diphenylnaphthopyran derivatives that are easy to prepare on a large scale has become a technical problem to be solved in the present invention

Method used

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  • Naphthapyran derivative containing sulfonamide groups
  • Naphthapyran derivative containing sulfonamide groups
  • Naphthapyran derivative containing sulfonamide groups

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Experimental program
Comparison scheme
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Embodiment 1

[0031] Synthesis of compound Nip-Me

[0032] (1) Synthesis of N-methyl-4-bromo-1,8-naphthalimide (compound shown in formula III-1):

[0033]

[0034] In a 250mL three-necked flask, add 4-bromo-1,8-naphthalene anhydride (10g, 36.1mmol) and 30% methylamine aqueous solution (150mL, 42.57g), heat up to 85°C, stir for about 40 minutes, and a yellow precipitate precipitates . After the reaction solution was cooled, it was suction filtered to obtain a yellow solid, and after vacuum drying, 8.23 ​​g of N-methyl-4-bromo-1,8-naphthalimide was obtained, with a yield of 78.6%.

[0035] (2) Synthesis of N-methyl-4-methoxy-1,8-naphthalimide (compound shown in formula IV-1)

[0036]

[0037] In a 250mL three-necked flask, add yellow N-methyl-4-bromo-1,8-naphthalimide (8.07g, 27.8mmol), sodium methoxide (14.02g, 0.26mol) and anhydrous methanol (100mL) in sequence , heated to reflux for 36 hours. After suction filtration, the filter cake was washed with dilute hydrochloric acid (10%)...

Embodiment 2

[0048] Synthesis of Compound Nip-Bu

[0049] (1) Synthesis of N-butyl-4-bromo-1,8-naphthalimide (compound shown in formula III-2)

[0050]

[0051] In a 500mL three-neck flask, add 4-bromo-1,8-naphthalene anhydride (10g, 30.1mmol) and n-butylamine (146.2g, 2mol), heat up to 85°C, stir for 40min, and a yellow precipitate precipitates out. After the reaction solution was cooled, it was suction filtered to obtain a yellow solid, and after vacuum drying, 7.3 g of the product (compound represented by formula III-2) was obtained, with a yield of 66%.

[0052] (2) Synthesis of N-butyl-4-methoxy-1,8-naphthalimide (compound shown in formula IV-2)

[0053]

[0054] In a 1000mL three-necked flask, yellow N-butyl-4-bromo-1,8-naphthalimide (7.2g, 21.7mmol), sodium methoxide (14.02g, 260mol) and anhydrous methanol (400mL) were successively added, Heated to reflux for 20h. Suction filtration, the filter cake was washed with dilute hydrochloric acid (10%), and then washed with water ...

Embodiment 3

[0064] Synthesis of Compound Nip-Ph

[0065] (1) Synthesis of 4-bromo-N-phenyl-1,8-naphthalimide (compound shown in formula III-3)

[0066]

[0067] In a 1000mL single-necked flask, add 4-bromo-1,8 naphthalene anhydride (7.2g, 26mmol), acetic acid (700mL) and freshly distilled aniline (24g, 0.26mmol) successively, under the protection of argon, heat, stir and reflux for 30min, During the reflux process, all the raw materials were dissolved in the acetic acid solution and turned into a brown transparent solution. After the reaction, cool to room temperature, pour the solution into 300mL of water, precipitate a yellow precipitate, let it stand overnight, and obtain a yellow solid by suction filtration. After the filter cake is washed with absolute ethanol (150mL×2), it is vacuum-dried to obtain 7.6g of Formula III The compound shown in -1 has a yield of 82%.

[0068] 1 H-NMR (400MHz, CDCl3, ppm): δ=7.31(d, J=7.9Hz, 2H, phenyl-H), 7.49(t, J=7.3Hz, 1H, phenyl-H), 7.56(t, J ...

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Abstract

The invention relates to a 2,2-di-phenyl-2H-naphth[1,2-b] pyran derivative containing sulfonamide groups. The derivative is prepared by carrying out four reactions on 4-bromine-1,8-anhydride naphthalene sequentially through aminolysis with cyclic anhydride, condensation with Williamson ether, cracking with Zeisel ether and rearrangement with Claisen. Under the irradiation of sunlight, the designed and synthesized diphenyl naphthpyran derivative can change to pink from no color, and after the derivative is put back to a dark place, the derivative changes to be colorless again, so that the photochromic phenomenon is obvious, and the derivative is a good photochromic compound. Relative to the traditional diphenyl naphthpyran derivative, the diphenyl naphthpyran derivative containing the sulfonamide groups has the advantages of simpler synthesis, fewer synthesis steps, low raw material cost, easy scale industrial production, and the like.

Description

technical field [0001] The invention relates to a naphthopyran derivative containing an imide group, in particular to a 2,2-bisphenyl-2H-naphtho[1,2-b]furan containing an imide group derivative. Background technique [0002] 2,2 bisphenyl-2H-naphtho[1,2-b]furan (2,2-bisphenyl-2H-naphtho[1,2-b]pyran) derivatives (hereinafter referred to as "diphenylnaphtho[1,2-b]pyran) "Pyran derivatives", whose parent structure is shown in the following formula) are a class of compounds with excellent photochromic properties. [0003] [0004] So far, the diphenylnaphthopyran derivatives that have been reported are: Campredon et al. introduced F at the 4', 4" position, and simultaneously introduced F, Cl and Br at the 6-position to obtain the compound (M.Campredon, et al ., J.Photochem.Photobiol.A., 2003, 159, 7-16); Favaro et al. introduced methoxy at 4', 4 "position, and simultaneously introduced methyl compound at 5,6 positions (G.Favaro , et al., J.Photochem.Photobiol.A., 2008, 196...

Claims

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Application Information

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IPC IPC(8): C09K9/02C07D491/06
Inventor 甘家安朱为宏宋立文陈尚军孙春雨吴玥于晖晖张琪凯
Owner SHANGHAI GANTIAN OPTICAL MATERIALS